METHYL 4-AMINO-6-INDOLECARBOXYLATE

METHYL 4-AMINO-6-INDOLECARBOXYLATE Property

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

METHYL 4-AMINO-6-INDOLECARBOXYLATE Chemical Properties,Usage,Production

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