Production Method 1

1301630-23-8

94-68-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ;  3 h, rt

Reference

Acylspiro[azetidine-cyclobutane] compounds for inhibiting monoacylglycerol lipase (MAGL) and their preparation

, World Intellectual Property Organization, , ,

Production Method 2

94-68-8

Reaction Conditions

1.1 Catalysts: Bis(1,5-cyclooctadiene)nickel ,  1,1′-(1,2-Ethanediyl)bis[1,1-bis(1-methylethyl)phosphine ;  18 h, 150 °C

Reference

Hydrogenation and N-alkylation of anilines and imines via transfer hydrogenation with homogeneous nickel compounds

Benitez-Medina, G. Eliad; Garcia, Juventino J., Dalton Transactions, 2019, 48(47), 17579-17587

Production Method 3

94-68-8

Reaction Conditions

1.1 Reagents: Ammonium formate Catalysts: Palladium Solvents: Acetonitrile ,  Water ;  1.3 h, rt

Reference

Reductive monoalkylation of aromatic and aliphatic nitro compounds and the corresponding amines with nitriles

Nacario, Ruel; Kotakonda, Shailaja; Fouchard, David M. D.; Tillekeratne, L. M. Viranga; Hudson, Richard A., Organic Letters, 2005, 7(3), 471-474

Production Method 4

94-68-8

Reaction Conditions

1.1 Reagents: Fuming sulfuric acid ;  pH 2.5
1.2 Catalysts: Zirconium dioxide (strontium hexaferrite/Fe 3O 4) ;  3 h, rt → 70 °C; 5.5 h, 75 °C
1.3 Reagents: Potassium hydroxide Solvents: Water ;  pH 7

Reference

Preparation of 3-ethylamino-p-methylphenol

, China, , ,

Production Method 5

557-66-4

94-68-8

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: 1807948-76-0 Solvents: Toluene ;  12 h, 80 °C
1.2 Reagents: Ethyl acetate

Reference

Nickel-Catalyzed Amination of Aryl Chlorides with Ammonia or Ammonium Salts

Green, Rebecca A.; Hartwig, John F., Angewandte Chemie, 2015, 54(12), 3768-3772

Production Method 6

120-66-1

94-68-8

Reaction Conditions

1.1 Reagents: Phenylsilane Solvents: Tetrahydrofuran ;  20 h, 50 °C; 50 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  1 h, rt

Reference

Chelating Bis(1,2,3-triazol-5-ylidene) Rhodium Complexes: Versatile Catalysts for Hydrosilylation Reactions

Nguyen, Thanh V. Q.; Yoo, Woo-Jin; Kobayashi, Shu, Advanced Synthesis & Catalysis, 2016, 358(3), 452-458

Production Method 7

94-68-8

Reaction Conditions

1.1 Catalysts: Triethylamine, hydrochloride ,  2313248-90-5 Solvents: Methanol ;  12 h, 120 °C

Reference

Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment

Deng, Danfeng; Hu, Bowen ; Zhang, Ziyu; Mo, Shengkai; Yang, Min ; et al, Organometallics, 2019, 38(9), 2218-2226

Production Method 8

94-68-8

Reaction Conditions

1.1 Reagents: Nickel

Reference

Facile N-alkylation of anilines with alcohols over Raney nickel under microwave irradiation

Jiang, Yu-Lin; Hu, Yu-Qiao; Feng, Shu-Qing; Wu, Ji-Shan; Wu, Zu-Wang; et al, Synthetic Communications, 1996, 26(1), 161-4

Production Method 9

94-68-8

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Tris(dibenzylideneacetone)dipalladium ,  Tricyclohexyl[(dicyclohexylphosphino)(2,4,6-trimethylphenyl)methylene]phosphine Solvents: Tetrahydrofuran ;  90 min, rt
1.2 Reagents: Sodium chloride Solvents: Water

Reference

Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos)

Rodstein, Ilja; Prendes, Daniel Sowa; Wickert, Leon; Paassen, Maurice; Gessner, Viktoria H., Journal of Organic Chemistry, 2020, 85(22), 14674-14683

Production Method 10

87875-79-4

68253-33-8

94-68-8

Reaction Conditions

1.1 Reagents: Phenylsilane Catalysts: Tris(pentafluorophenyl)borane Solvents: Toluene-d8 ;  20 h, rt
1.2 Reagents: Hydrochloric acid Solvents: tert-Butyl methyl ether ,  Water ;  12 h, rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  4 h, rt

Reference

Mild reductive rearrangement of oximes and oxime ethers to secondary amines with hydrosilanes catalyzed by B(C6F5)3

Fang, Huaquan; Wang, Guoqiang; Oestreich, Martin, Organic Chemistry Frontiers, 2021, 8(13), 3280-3285

Production Method 11

120-66-1

94-68-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: p-Toluenesulfonic acid ,  Boron trifluoride etherate ,  (OC-6-33)-Carbonyl[1,1′-[2-[(diphenylphosphino-κP)methyl]-2-methyl-1,3-propanedi… Solvents: Tetrahydrofuran ;  16 h, 50 atm, 120 °C

Reference

Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines

Yuan, Ming-Lei; Xie, Jian-Hua; Zhou, Qi-Lin, ChemCatChem, 2016, 8(19), 3036-3040

Production Method 12

94-68-8

Reaction Conditions

1.1 Catalysts: Platinum ,  Titania Solvents: Ethanol ;  150 min, 25 °C

Reference

Factors affecting the selectivity of the photocatalytic conversion of nitroaromatic compounds over TiO2 to valuable nitrogen-containing organic compounds

Hakki, Amer; Dillert, Ralf; Bahnemann, Detlef W., Physical Chemistry Chemical Physics, 2013, 15(8), 2992-3002

Production Method 13

94-68-8

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid ,  Sulfuric acid ,  Phosphorus trichloride

Reference

Bulk-scale preparation of ethyl 2-[3,6-bis(N-ethylamino)-2,7-dimethyl-3-hydroxanth-9-yl]benzoate hydrochloride

, China, , ,

Production Method 14

94-68-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol

Reference

Preparation of aromatic secondary amines from nitro compounds and nitriles

, Japan, , ,

Production Method 15

94-68-8

Reaction Conditions

1.1 Reagents: Sodium

Reference

N-Ethylpiperidine

Wollensak, J.; Closson, R. D., Organic Syntheses, 1963, 43, 45-8

Production Method 16

74965-31-4

94-68-8

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran
1.2 -
1.3 Reagents: Hydrochloric acid Solvents: Water

Reference

Selective monoalkylation of amines

Dalla Croce, Piero; La Rosa, Concetta; Ritieni, Alberto, Journal of Chemical Research, 1988, (10), 346-7

Production Method 17

94-68-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  24 h, 20 °C

Reference

Selective N-alkylation of amines using nitriles under hydrogenation conditions: facile synthesis of secondary and tertiary amines

Ikawa, Takashi; Fujita, Yuki; Mizusaki, Tomoteru; Betsuin, Sae; Takamatsu, Haruki; et al, Organic & Biomolecular Chemistry, 2012, 10(2), 293-304

Production Method 18

94-68-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Borate(1-), tetrafluoro-, cobalt(2+) (2:1) ,  1671080-01-5 Solvents: 1,4-Dioxane ;  24 h, 40 bar, 100 °C

Reference

Tailored Cobalt-Catalysts for Reductive Alkylation of Anilines with Carboxylic Acids under Mild Conditions

Liu, Weiping; Sahoo, Basudev; Spannenberg, Anke; Junge, Kathrin; Beller, Matthias, Angewandte Chemie, 2018, 57(36), 11673-11677

Production Method 19

94-68-8

Reaction Conditions

1.1 Reagents: Hydrogen ,  Polyethylene glycol mono(4-tert-octylphenyl) ether Catalysts: Palladium ,  Lipase CaLB (Candida antarctica) ;  12 h, 25 °C

Reference

A facile, one-pot reductive alkylation of aromatic and heteroaromatic amines in aqueous micellar media: a chemoenzymatic approach

Ganesh, Krithika; Sambasivam, Ganesh; S, Karthikeyan, Organic & Biomolecular Chemistry, 2023, 21(20), 4264-4268

Production Method 20

94-68-8

Reaction Conditions

1.1 Reagents: Ammonium formate Catalysts: Palladium Solvents: Isopropanol ,  Water ;  5 min, rt
1.2 45 min, rt

Reference

On the asymmetric iridium-catalyzed N-allylation of amino acid esters: Improved selectivities through structural variation of the chiral phosphoramidite ligand

Albat, Dominik; Kocher, Alicia; Witt, Julia; Schmalz, Hans-Guenther, European Journal of Organic Chemistry, 2022, 2022(12),

N-Ethyl-o-toluidine Raw materials

• N-(tert-Butoxycarbonyl)-2-methylaniline
• Ethylamine hydrochloride
• ETHANONE, 1-(2-METHYLPHENYL)-, OXIME, (Z)-
• o-Methylacetanilide
• ETHANONE, 1-(2-METHYLPHENYL)-, OXIME, (E)-
• 1,1-Dimethylethyl N-ethyl-N-(2-methylphenyl)carbamate

N-Ethyl-o-toluidine Preparation Products

• N-Ethyl-o-toluidine (94-68-8)

• 1. An intramolecular tryptophan-condensation approach for peptide stapling?
  Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. Johannes Org. Biomol. Chem., 2018,16, 389-392
• 2. An all-solid-state imprinted polymer-based potentiometric sensor for determination of bisphenol S?
  Rongning Liang,Tanji Yin,Ruiqing Yao,Wei Qin RSC Adv., 2016,6, 73308-73312
• 3. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782
• 4. An amorphous Cu–In–S nanoparticle-based precursor ink with improved atom economy for CuInSe2 solar cells with 10.85% efficiency?
  Green Chem., 2017,19, 1268-1277
• 5. 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

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Aminotoluenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Toluenes Aminotoluenes
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

• 78376-90-6(n-(2,6-dimethylphenyl)aziridine)
• 2100-43-8(2-methyl-N-(propan-2-yl)aniline)
• 63134-14-5(1,3-Benzenediamine,N3-ethyl-4-methyl-)
• 6387-29-7((4-Amino-2-methylphenyl)ethylamine)
• 21702-27-2(1,2-Ethanediamine,N1-(2-methylphenyl)-)
• 78376-89-3(n-(2,4-dimethylphenyl)aziridine)
• 356532-66-6(Benzenamine, 2,4-dimethyl-N-propyl- (9CI))
• 134030-21-0(N,N'-Bis(2,4,6-trimethylphenyl)ethane-1,2-diamine)
• 769-23-3(Benzenamine, N-ethyl-2,6-dimethyl-)
• 13519-76-1(N-ethyl-2,5-dimethylaniline)