METHYL 4-AMINO-6-INDOLECARBOXYLATE Chemical Properties

Melting point:

160-163 °C(Solv: benzene (71-43-2))

Boiling point:

429.8±25.0 °C(Predicted)

Density 

1.339±0.06 g/cm3(Predicted)

storage temp. 

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

pka

17.03±0.30(Predicted)

Appearance

Light brown to brown Solid

CAS DataBase Reference

121561-15-7(CAS DataBase Reference)

METHYL 4-AMINO-6-INDOLECARBOXYLATE Usage And Synthesis

Uses

In the pharmaceutical field, methyl 4-amino-6-indolecarboxylate is mainly used as an organic synthesis intermediate to synthesize a variety of drug compounds, such as methyl 4-amino-6-indolecarboxylate hydrochloride, which is used in drug synthesis.

Synthesis

To a solution of methyl 4-[(E)-2-(dimethylamino)vinyl]-3,5-dinitrobenzoate (D200) (10 g, 34 mmol, 1 eq.) in methanol (250 ml) was added 10% palladium charcoal (50% wet, 1.0 g, 5% w/w). The reaction mixture was stirred under hydrogen atmosphere for 7 hours. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure. The residue was ground with ethyl acetate/isohexane mixed solvent to afford methyl 4-amino-1H-indole-6-carboxylate (D201) (5 g, 77% yield) as a dark pink solid. Mass spectrometry analysis showed [M+H]+ = 191.0 and retention time (RT) = 1.20 min.

References

[1] Tetrahedron Letters, 2007, vol. 48, # 45, p. 7990 - 7993
[2] Patent: WO2004/50619, 2004, A1. Location in patent: Page 57
[3] Patent: WO2005/58915, 2005, A1. Location in patent: Page/Page column 18

METHYL 4-AMINO-6-INDOLECARBOXYLATE(121561-15-7)Related Product Information

• 4-BENZYLOXY-6-INDOLE CARBOXYLIC ACID METHYL ESTER
• 4-HYDROXY-1H-INDOLE-6-CARBOXYLIC ACID METHYL ESTER
• 1H-Indole-6-carboxylic acid, 4-chloro-, Methyl ester
• 1H-Indole, 4-broMo-6-chloro-
• 1H-Indole-6-carboxylic acid, 4-fluoro-, Methyl ester
• METHYL 4-CHLORO-3-METHYLBENZOATE
• METHYL 4-[(4-METHYLPIPERAZIN-1-YL)METHYL]BENZOATE
• METHYL 4-(TRIFLUOROMETHYL)NICOTINATE
• METHYL 4-BROMO-2-BROMOMETHYL-BENZOATE
• 1H-Indole, 4-broMo-6-(phenylMethoxy)-
• 4-NITRO-6-INDOLECARBOXYLIC ACID METHYL ESTER
• METHYL 6-AMINO-4-INDOLECARBOXYLATE,Methyl 6-Amino-4-indolecarboxylate Hydrochloride
• Indole-6-carboxylic acid
• Methyl indole-6-carboxylate
• 6-HYDROXYMETHYLINDOLE
• Indole-6-carboxaldehyde
• 4-Aminoindole
• METHYL 4-AMINO-6-INDOLECARBOXYLATE