1-METHYL-1H-INDOL-4-AMINE Chemical Properties

Boiling point:

328.0±15.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

5.04±0.10(Predicted)

form 

solid

Appearance

Brown to black Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

1-METHYL-1H-INDOL-4-AMINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-amino-N-methylindole from 1-methyl-4-nitro-1H-indole: Reduced iron powder (3.36 g, 60 mmol) was added batchwise to a boiling mixture containing 1-methyl-4-nitro-1H-indole (40 mmol), concentrated hydrochloric acid (5 mL) and ethanol (100 mL). The resulting suspension was refluxed for 1 h. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was neutralized with ammonia, filtered to remove iron residue, and washed with ethanol (30 mL). The filtrate was evaporated and concentrated, then diluted with ethyl acetate (100 mL). The organic phase was washed sequentially with brine (25 mL) and water (2 x 50 mL), dried with magnesium sulfate, and the solvent was evaporated to give the residue 1-methyl-1H-indol-4-ylamine (7). The product was a gray solid with a melting point of 95-96 °C in 85% yield.1H NMR (300 MHz, CDCl3) δ 7.02 (t, 1H, J = 7.8 Hz, H-6), 6.86 (d, 1H, J = 3.3 Hz, H-2), 6.74 (d, 1H, J = 8.7 Hz, H-5), 6.33 (d, 1H, J = 8.7 Hz , H-7), 6.32 (d, 1H, J = 3.3 Hz, H-3), 3.82 (br s, 2H, NH2-4), 3.61 (s, 3H, CH3-1). Calculated values for elemental analysis (C9H10N2): C, 73.94; H, 6.89; N, 19.16; measured values: C, 73.80; H, 6.80; N, 19.30%.

References

[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 871 - 887
[2] Tetrahedron Letters, 2017, vol. 58, # 13, p. 1324 - 1325
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 9, p. 3417 - 3427
[4] Journal of Medicinal Chemistry, 1993, vol. 36, # 8, p. 1104 - 1107
[5] Patent: US2009/227575, 2009, A1. Location in patent: Page/Page column 21; 17

1-METHYL-1H-INDOL-4-AMINE(85696-95-3)Related Product Information

• 5-METHOXY-1-METHYL-4-NITROINDOLE-3-CARBOXALDEHYDE
• 1-BOC-4-AMINOINDOLE
• 1-METHYL-1H-INDOL-4-AMINE
• 3-Methyl-1H-indol-1-amine
• 1-METHYL-1H-INDOL-5-AMINE
• 2,3-Dihydro-2-methyl-1H-indol-1-amine hydrochloride
• 2,3-dihydro-2-methyl-1h-indol-1-amine
• 2-METHYL-1H-INDOL-5-AMINE
• 1-Methylindole
• (4-TERT-BUTOXYCARBONYLAMINO-INDOL-1-YL)-ACETIC ACID
• 4-AMINO-5-METHOXY-1,2-DIMETHYL-1H-INDOLE-3-CARBOXYLIC ACID ETHYL ESTER
• 4-[1-(4-TERT-BUTOXYCARBONYL-BENZYL)-1H-INDOL-4-YL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 3-(4-TERT-BUTOXYCARBONYLAMINO-INDOL-1-YL)-PROPIONIC ACID
• 3-ethyl-2-methyl-1H-indol-5-amine
• 2,3-dihydro-2-methyl-1H-indol-1-amine monomethanesulphonate
• 1-ETHYL-2-METHYL-1H-INDOL-5-AMINE
• RARECHEM AL BL 1482
• RARECHEM AL BD 1521