Production Method 1

120-94-5

96-54-8

Reaction Conditions

1.1 Reagents: Alumina ,  Mercuric chloride Catalysts: Palladium

Reference

Aromatizing saturated nitrogen-containing heterocyclics

, Federal Republic of Germany, , ,

Production Method 2

96-54-8

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Tetrabutylammonium bromide

Reference

Selective alkylation of pyrrole by phase transfer catalysis in the absence of solvent

Diez-Barra, E.; de la Hoz, A.; Loupy, A.; Sanchez-Migallon, A., Journal of Heterocyclic Chemistry, 1994, 31(6), 1715-17

Production Method 3

96-54-8

Reaction Conditions

1.1 Catalysts: 2839377-58-9 ;  18 h, rt

Reference

Solvent/metal-free benzimidazolium-based carboxyl-functionalized porphyrin photocatalysts for the room-temperature alkylation of amines under the irradiation of visible light

Raut, Subodh Uttamrao; Balinge, Kamlesh Rudreshwar; Deshmukh, Shubham Avinash; Barange, Shital Haribhau; Mataghare, Bhairav Chandroday; et al, Catalysis Science & Technology, 2022, 12(19), 5917-5931

Production Method 4

120-94-5

96-54-8

Reaction Conditions

1.1 Reagents: 3,3-Dimethyl-1-butene ,  Sodium tert-butoxide Catalysts: (SP-5-54)-[2-[[Bis(1-methylethyl)phosphino-κP]oxy]-6-[[bis(1-methylethyl)phosphi… Solvents: p-Xylene ;  12 h, 150 °C

Reference

Selective Catalytic Transfer Dehydrogenation of Alkanes and Heterocycles by an Iridium Pincer Complex

Yao, Wubing; Zhang, Yuxuan; Jia, Xiangqing; Huang, Zheng, Angewandte Chemie, 2014, 53(5), 1390-1394

Production Method 5

6973-60-0

96-54-8

Reaction Conditions

1.1 Reagents: N-Methyl-2-pyrrolidone Catalysts: Silver acetate ,  Potassium carbonate ;  16 h, 120 °C

Reference

Comparative Study of Copper- and Silver-Catalyzed Protodecarboxylations of Carboxylic Acids

Goossen, Lukas J.; Rodriguez, Nuria; Linder, Christophe; Lange, Paul P.; Fromm, Andreas, ChemCatChem, 2010, 2(4), 430-442

Production Method 6

17171-45-8

96-54-8

Reaction Conditions

1.1 Solvents: Methanol ,  Water ;  20 min, 70 °C

Reference

N-methylimidazole

Tindall, Craig; Ladd, Carolyn L., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2014, 1, 1-13

Production Method 7

96-54-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Tetrahydrofuran ;  5 h, 40 °C

Reference

Antiinflammatory COX/LOX inhibitor and its preparation method and application

, China, , ,

Production Method 8

4637-24-5

96-54-8

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  rt; 4 h, 90 °C

Reference

Alkylation method of nitrogen-containing hydrogen compound and its application

, China, , ,

Production Method 9

4277-63-8

96-54-8

Reaction Conditions

1.1 Catalysts: N′′′-(1,1-Dimethylethyl)-N,N,N′,N′,N′′,N′′-hexamethylphosphorimidic triamide Solvents: Tetrahydrofuran ;  22.5 h, 393 K

Reference

The reaction of pyrrole with dimethyl carbonate under phosphazene catalysis: N-methoxycarbonylation vs N-methylation

Quaranta, Eugenio; Carafa, Marianna; Trani, Francesca, Applied Catalysis, 2009, 91(1-2), 380-388

Production Method 10

96-54-8

Reaction Conditions

1.1 Reagents: Potassium superoxide Catalysts: 18-Crown-6 Solvents: Tetrahydrofuran ;  1 h
1.2 1 h

Reference

Potassium superoxide

Johnson, Roy A., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007, 1, 1-8

Production Method 11

96-54-8

Reaction Conditions

1.1 Reagents: Potassium superoxide Catalysts: 18-Crown-6 Solvents: Tetrahydrofuran
1.2 -

Reference

Ultrasound promoted N-alkylation of pyrrole using potassium superoxide as base in crown ether

Yim, Eui Soon; Park, Moon Kyeu; Han, Byung Hee, Ultrasonics Sonochemistry, 1997, 4(2), 95-98

Production Method 12

96-54-8

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Tetrabutylammonium bromide

Reference

Phase transfer catalysis without solvent. Use of alkyl iodides

Diez-Barra, E.; De la Hoz, A.; Sanchez-Migallon, A.; Sanchez-Verdu, P.; Bram, G.; et al, Synthetic Communications, 1989, 19(1-2), 293-6

Production Method 13

638-37-9

96-54-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ;  -5 °C; rt → 45 °C; 14 h, 45 °C

Reference

Method for synthesizing N-methylpyrrole using succinaldehyde

, China, , ,

Production Method 14

96-54-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide Catalysts: 1H-Pyrrole-2-carboxylic acid, 1-methyl-, methyl ester Solvents: Dichloromethane ;  rt
1.2 3 h, rt → reflux

Reference

Preparation of catalysts for production of N-alkylpyrrole derivatives

, China, , ,

Production Method 15

96-54-8

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: 1-Butyl-3-methylimidazolium hexafluorophosphate Solvents: 1-Butyl-3-methylimidazolium hexafluorophosphate ;  2 h, 40 °C

Reference

Synthesis of N-substituted pyrrole in ionic liquid

, China, , ,

Production Method 16

96-54-8

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: 1-Butyl-3-methylimidazolium hexafluorophosphate ;  2 h, 40 °C

Reference

Organic reactions in ionic liquids. A simple and highly regioselective N-substitution of pyrrole

Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qin-Guo, Synthesis, 2004, (12), 1951-1954

Production Method 17

120-94-5

96-54-8

Reaction Conditions

1.1 Catalysts: Alumina ,  Platinum

Reference

Platinum on alumina

King, Anthony O.; Shinkai, Ichiro, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 18

4637-24-5

96-54-8

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  4 h, 90 °C

Reference

N-alkylation of N-H compounds in N, N-dimethylformamide dialkyl acetal

Zhao, Hui; Zhu, Xiaoyun; Hu, Xiaoxia; Liu, Yan-ge; Tang, Chunlei; et al, Youji Huaxue, 2019, 39(2), 434-442

Production Method 19

109719-76-8

96-54-8

Reaction Conditions

1.1 Solvents: Acetic anhydride

Reference

Synthesis of N-alkylpyrroles

Kreher, R.; Pawelczyk, H., Angewandte Chemie, 1964, 76(12),

Production Method 20

96-54-8

Reaction Conditions

Reference

Preparation of stachydrinol and N-methylprolinol salts from piperidine. I

Lukes, Rudolf; Cervinka, Otakar, Chemicke Listy pro Vedu a Prumysl, 1953, 47, 392-8

N-Methylpyrrole Raw materials

• (dimethoxymethyl)dimethylamine
• methyl pyrrole-1-carboxylate
• Sulfur, hydroxytrimethyl- (8CI)
• 1-methyl-1H-pyrrole-2-carboxylic acid
• 1-Methylpyrrolidine
• 1H-Pyrrole, 2,5-dihydro-1-methyl-, 1-oxide
• butanedial

N-Methylpyrrole Preparation Products

• N-Methylpyrrole (96-54-8)

• 1. Fate of single walled carbon nanotubes in wetland ecosystems?
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  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrroles N-methylpyrroles
• Solvents and Organic Chemicals Organic Compounds Heterocyclic Compounds

• 33804-84-1(2-methyl-2H-Isoindole)
• 2350-76-7(1-Methylpyridin-1-ium bromide)
• 930-73-4(1-Methylpyridin-1-ium iodide)
• 7680-73-1(1-Methyl-pyridinium Chloride)
• 694-56-4(Pyridinium, 1-methyl-)
• 190386-37-9(N-Methylpyrrole-d4 (ring-d4))
• 92933-61-4(1H-Pyrrole, ethyl-)
• 617-92-5(1-Ethylpyrrole)
• 20687-13-2(N-Methyl-d3-pyrrole)
• 72160-99-7(1,4-Diazocine, 1,4-dihydro-1,4-dimethyl-)