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121561-15-7

121561-15-7 Structure

121561-15-7 Structure
IdentificationMore
[Name]

METHYL 4-AMINO-6-INDOLECARBOXYLATE
[CAS]

121561-15-7
[Synonyms]

4-AMINO-6-METHOXYCARBONYL INDOLE
4-AMino-6-Methylcarboxylateindole
Methyl 4-AMinoindole-6-carboxylate
METHYL 4-AMINO-6-INDOLECARBOXYLATE
Methyl 4-AMino-6-indolecarboxylate Hy
Methyl4-amino-1H-indole-6-carboxylate
4-AMINOINDOLE-6-CARBOXYLIC ACID METHYL ESTER
METHYL 4-AMINO-6-INDOLECARBOXYLATE USP/EP/BP
4-AMINO-6-INDOLE CARBOXYLIC ACID METHYL ESTER
Methyl 4-Amino-6-indolecarboxylate Hydrochloride
4-amino-6-indole carboxylic acid methyl ester ,95%
1H-Indole-6-carboxylic acid, 4-aMino-, Methyl ester
1H-Indole-6-carboxylicacid,4-amino-,methylester(9CI)
4-amino-1H-indole-6-carboxylic acid methyl ester hydrochloride
[Molecular Formula]

C10H10N2O2
[MDL Number]

MFCD00461176
[Molecular Weight]

190.2
[MOL File]

121561-15-7.mol
Chemical PropertiesBack Directory
[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)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Methanol-->Sulfuric acid-->N,N-Dimethylformamide-->Thionyl chloride-->Nitric acid-->Palladium-->N,N-Dimethylformamide dimethyl acetal-->Cuprous iodide-->p-Toluic acid-->(E)-Methyl 4-(2-(diMethylaMino)vinyl)-3,5-dinitrobenzoate
Hazard InformationBack Directory
[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]

(E)-Methyl 4-(2-(diMethylaMino)vinyl)-3,5-dinitrobenzoate

597562-13-5

METHYL 4-AMINO-6-INDOLECARBOXYLATE

121561-15-7

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
Spectrum DetailBack Directory
[Spectrum Detail]

METHYL 4-AMINO-6-INDOLECARBOXYLATE(121561-15-7)1HNMR
METHYL 4-AMINO-6-INDOLECARBOXYLATE(121561-15-7)1HNMR
METHYL 4-AMINO-6-INDOLECARBOXYLATE(121561-15-7)13CNMR
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