Production Method 1

29124-57-0

877-42-9

Reaction Conditions

1.1 Catalysts: Sodium tert-butoxide ,  [1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]chloroc… Solvents: Toluene ;  8 h, 70 °C

Reference

Synthesis of quinolines and naphthyridines via catalytic retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes or nicotinaldehydes

Zhang, Song-Lin; et al, Organic & Biomolecular Chemistry, 2016, 14(38), 8966-8970

Production Method 2

42835-98-3

877-42-9

Reaction Conditions

1.1 Catalysts: Tris(2,2′-bipyridyl)ruthenium(II) chloride ,  Cobalt, bis[[2,3-butanedione di(oximato-κN)](1-)]chloro(pyridine)-, (OC-6-42)- Solvents: Ethanol ;  24 h, 30 °C

Reference

Acceptorless Dehydrogenation of N-Heterocycles by Merging Visible-Light Photoredox Catalysis and Cobalt Catalysis

He, Ke-Han; et al, Angewandte Chemie, 2017, 56(11), 3080-3084

Production Method 3

42835-98-3

877-42-9

Reaction Conditions

1.1 Catalysts: Tris(pentafluorophenyl)borane Solvents: p-Xylene ;  22 h, 150 °C

Reference

Tris(pentafluorophenyl)borane-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles

Kojima, Masahiro; et al, Angewandte Chemie, 2016, 55(40), 12224-12227

Production Method 4

877-42-9

Reaction Conditions

1.1 Reagents: Acetic acid ,  Hydrochloric acid Solvents: Water ;  0.5 h, 100 °C
1.2 Reagents: Potassium ,  Iodine Solvents: Toluene
1.3 Solvents: Toluene ;  1 h, 100 °C; 6 h, 100 °C; 100 °C → rt
1.4 Reagents: Ammonia Solvents: Water ;  basified

Reference

A Convenient Organic-Inorganic Hybrid Approach Toward Highly Stable Squaraine Dyes with Reduced H-Aggregation

Yan, Zhengquan; et al, Advanced Functional Materials, 2012, 22(2), 345-352

Production Method 5

877-42-9

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Alumina ,  Hydrochloric acid ;  10 min

Reference

One-pot synthesis of quinaldine derivatives by using microwave irradiation without any solvent - A green chemistry approach

Safari, Javad; et al, Journal of Chemical Sciences (Bangalore, 2009, 121(4), 481-484

Production Method 6

1253423-96-9

877-42-9

Reaction Conditions

1.1 Reagents: Acetic acid ,  Iron ;  2 h, reflux

Reference

Iron/acetic acid-mediated carbon degradation: a facile route for the synthesis of quinoline derivatives

Ramesh, Chintakunta; et al, Tetrahedron Letters, 2010, 51(40), 5234-5237

Production Method 7

78782-17-9

6563-11-7

877-42-9

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Toluene ;  3 h, 80 °C
1.2 Reagents: Sodium peroxoborate Solvents: Tetrahydrofuran ,  Water ;  3 h, rt
1.3 Reagents: Sodium chloride Solvents: Water ;  rt

Reference

Transition-Metal-Free Regioselective Alkylation of Pyridine N-Oxides Using 1,1-Diborylalkanes as Alkylating Reagents

Jo, Woohyun; et al, Angewandte Chemie, 2016, 55(33), 9690-9694

Production Method 8

877-42-9

Reaction Conditions

1.1 Catalysts: Titania Solvents: Ethanol ;  5 min; 72 h, rt

Reference

Preparation of 2-alkylquinolines by TiO2-photocatalyzed reaction of arylamines in alcohols

Matsui, Masaki; et al, Shikizai Kyokaishi, 2002, 75(7), 319-323

Production Method 9

103-88-8

877-42-9

Reaction Conditions

1.1 Reagents: Cupric acetate Catalysts: Silver hexafluoroantimonate ,  Bis(dichloro(η6-p-cymene)ruthenium) Solvents: 1,4-Dioxane ;  20 h, 140 °C

Reference

Carboxylate-assisted ruthenium(II)-catalyzed C-H activations of monodentate amides with conjugated alkenes

Li, Jie; et al, Organic Chemistry Frontiers, 2015, 2(9), 1035-1039

Production Method 10

877-42-9

877-42-9

Reaction Conditions

1.1 Reagents: Sodium borohydride Catalysts: Nickel dichloride Solvents: Methanol ;  0 °C; 4 h, rt
2.1 Reagents: Potassium tert-butoxide ,  Oxygen Catalysts: 1,10-Phenanthroline ,  Tempo ,  Nickel bromide Solvents: 2-Methyl-2-butanol ;  48 h, 95 °C

Reference

Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen

Bera, Sourajit; et al, Organic Letters, 2020, 22(16), 6458-6463

Production Method 11

877-42-9

Reaction Conditions

1.1 Catalysts: 12-Tungstophosphoric acid ;  12 min

Reference

Synthesis of quinaldines and lepidines by a Doebner-Miller reaction under thermal and microwave irradiation conditions using phosphotungstic acid

Sivaprasad, Ganesabaskaran; et al, Tetrahedron Letters, 2006, 47(11), 1783-1785

Production Method 12

877-42-9

Reaction Conditions

1.1 Reagents: Acetic acid ,  Hydrochloric acid Solvents: Toluene ,  Water ;  0.5 h, 100 °C
1.2 Catalysts: Iodine ,  Potassium iodide Solvents: Toluene ;  1 h, 100 °C; 6 h, 100 °C; 100 °C → rt
1.3 Reagents: Ammonia Solvents: Water ;  basified, rt

Reference

Near-Infrared Absorbing Squaraine Dyes for Solar Cells: Relationship between Architecture and Performance

Yan, Zhengquan; et al, Journal of Physical Chemistry C, 2012, 116(16), 8894-8900

Production Method 13

877-42-9

Reaction Conditions

1.1 Catalysts: Cobalt, bis[[2,3-butanedione di(oximato-κN)](1-)]chloro(pyridine)-, (OC-6-42)- ,  Ruthenium(2+), tris(1,10-phenanthroline-κN1,κN10)-, (OC-6-11)-, hexafluorophosph… Solvents: Acetonitrile ,  Water ;  12 h, rt

Reference

Photocatalytic Synthesis of Quinolines via Povarov Reaction under Oxidant-Free Conditions

Su, Long-Long; et al, Organic Letters, 2022, 24(5), 1180-1185

Production Method 14

877-42-9

Reaction Conditions

1.1 Catalysts: Hydrochloric acid Solvents: Water ;  rt → 100 °C; 20 min, 100 °C
1.2 Catalysts: Hydrochloric acid Solvents: Toluene ;  3 h, 100 °C
1.3 Reagents: Ammonia Solvents: Water ;  pH 7 - 8, rt

Reference

Synthesis of styrylquinoline derivatives and evaluation of their antitumor activities

Wang, Ming; et al, Jingxi Huagong, 2015, 32(10), 1132-1136

Production Method 15

877-42-9

Reaction Conditions

1.1 Catalysts: Acetic acid ;  3 - 4 h, 25 °C; 3.5 - 4 h, reflux
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized

Reference

High throughput one pot synthesis of 2-methylquinolines

Chandrashekarappa, Kiran Kumar H.; et al, Tetrahedron Letters, 2013, 54(11), 1368-1370

Production Method 16

2065-66-9

6563-11-7

877-42-9

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: tert-Butyl methyl ether ;  rt; 3 h, 80 °C

Reference

Reductive C2-Alkylation of Pyridine and Quinoline N-Oxides Using Wittig Reagents

Han, Sangil; et al, Angewandte Chemie, 2018, 57(39), 12737-12740

Production Method 17

914264-22-5

877-42-9

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Benzene ;  5 h, reflux
1.2 Reagents: Potassium carbonate ;  neutralized

Reference

The peculiar reaction of 2-arylazo-1-vinylpyrroles with trifluoroacetic acid: a novel synthesis of 2-methylquinolines

Schmidt, Elena Yu.; et al, Tetrahedron, 2009, 65(25), 4855-4858

Production Method 18

877-42-9

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Copper oxide (CuO) ,  Chromium iron oxide (Cr2FeO4) ,  Titania Solvents: Water ;  6 - 24 h, 25 °C

Reference

Photocatalytic tandem reaction of primary alcohols with arylamines in the synthesis of amides and alkylquinolines in the presence of a heterogeneous Fe(CrO2)2-TiO2/X system under aerobic conditions

Makhmutov, A. R., Russian Chemical Bulletin, 2019, 68(1), 68-73

Production Method 19

78782-17-9

5332-25-2

877-42-9

Reaction Conditions

1.1 Reagents: Dimethylzinc ,  Lithium tert-butoxide Solvents: Toluene ;  3 h, 120 °C

Reference

ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism

Jo, Woohyun; et al, Journal of the American Chemical Society, 2020, 142(30), 13235-13245

Production Method 20

877-42-9

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Benzene ;  5 h, reflux
1.2 Reagents: Potassium carbonate ;  neutralized

Reference

The peculiar reaction of 2-arylazo-1-vinylpyrroles with trifluoroacetic acid: a novel synthesis of 2-methylquinolines

Schmidt, Elena Yu.; et al, Tetrahedron, 2009, 65(25), 4855-4858

Production Method 21

872-36-6

877-42-9

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Catalysts: Rhodium(2+), tris(acetonitrile)[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopen… Solvents: Isopropanol ;  12 h, 140 °C
1.2 Reagents: Ammonium hydroxide Solvents: Water ;  basified, cooled

Reference

Rhodium-Catalyzed C-H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon

Nan, Jiang ; et al, Organic Letters, 2021, 23(22), 8910-8915

Production Method 22

877-42-9

68254-64-8

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Palladium ,  Palladium chloride Solvents: Acetonitrile ;  24 h, 80 °C

Reference

Assembly of Substituted 2-Alkylquinolines by a Sequential Palladium-Catalyzed C-N and C-C Bond Formation

Matsubara, Yoshio; et al, Angewandte Chemie, 2011, 50(33), 7670-7673

Production Method 23

42835-98-3

877-42-9

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide ,  Oxygen Catalysts: 1,10-Phenanthroline ,  Tempo ,  Nickel bromide Solvents: 2-Methyl-2-butanol ;  48 h, 95 °C

Reference

Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen

Bera, Sourajit; et al, Organic Letters, 2020, 22(16), 6458-6463

6-Bromo-2-methylquinoline Raw materials

• methyl(triphenyl)phosphonium;iodide
• 2-Amino-5-bromobenzaldehyde
• Bis[(pinacolato)boryl]methane
• 6-Bromoquinoline
• N-(4-bromophenyl)acetamide
• Vinylene carbonate
• 6-Bromo-2-methylquinoline
• 6-Bromo-2-methyl-1,2,3,4-tetrahydroquinoline
• 2-Pentanone, 4-(5-bromo-2-nitrophenyl)-5-nitro-
• 2-[2-(4-Bromophenyl)diazenyl]-1-ethenyl-5-methyl-1H-pyrrole
•  

6-Bromo-2-methylquinoline Preparation Products

• 6-Bromo-2-methylquinoline (877-42-9)
• N-Ethyl-4-bromo-benzenamine (68254-64-8)

• 1. An ionic liquid-mesoporous silica blend as a novel adsorbent for the adsorption and recovery of palladium ions, and its applications in continuous flow study and as an industrial catalyst?
  Shivani Sharma,Chia-Ming Wu,Ranjit T. Koodali,N. Rajesh RSC Adv., 2016,6, 26668-26678
• 2. An anti-leakage liquid metal thermal interface material
  Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng Chu RSC Adv., 2020,10, 18824-18829
• 3. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 4. An aptamer-based keypad lock system?
  Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang Wang Chem. Commun., 2012,48, 802-804
• 5. An antioxidative galactomannan extracted from Chinese Sesbania cannabina enhances immune activation of macrophage cells?
  Chongyang Zhu,Xiaojia Bian,Xin Jia,Ning Tang,Yongqiang Cheng Food Funct., 2020,11, 10635-10644

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Haloquinolines

• 1075-34-9(5-bromo-2-methyl-1H-indole)
• 103858-50-0(Quinoline, 7-bromo-2,4-dimethyl-)
• 50488-44-3(4-Bromo-2-methylquinoline)
• 6127-19-1(6-Bromo-2-methyl-1h-indole)
• 1070879-54-7(4,7-dibromo-2-methylquinoline)
• 54408-52-5(5-Bromo-2-methylquinoline)
• 1070879-53-6(4,6-dibromo-2-methylquinoline)
• 61047-43-6(8-Bromo-2-methylquinoline)
• 4965-34-8(7-Bromo-2-methylquinoline)
• 6127-18-0(4-Bromo-2-methyl-1H-indole)