HCID 85206179, compound → Ethyl 6-amino-1H-indole-7-carboxylate

HRID 2404692Notes

Reaction equation

HRID 2404692 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[C:7]([CH:14]=[CH:15]N(C)C)[C:6]=1[N+:19]([O-])=O)[CH3:2]>CCO.[Ni]>[CH2:1]([O:3][C:4]([C:5]1[C:10]([NH2:11])=[CH:9][CH:8]=[C:7]2[C:6]=1[NH:19][CH:15]=[CH:14]2)=[O:22])[CH3:2]

Participants

4

Reactant 1

HCID 85206179HCID 85206179, compound

Product 1

HCID 10822051Ethyl 6-amino-1H-indole-7-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(2-dimethylamino-vinyl)-2,6-dinitro-benzoic acid ethyl ester (30 g, 0.097 mol) and Raney Ni (10 g) in EtOH (1000 mL) was stirred under H2 (50 psi) for 2 h. The catalyst was filtered off, and the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel to give 6-amino-1H-indole-7-carboxylic acid ethyl ester (B-19) as an off-white solid (3.2 g, 16%). 1H NMR (DMSO-d6) δ 10.38 (s, 1H), 7.44-7.41 (d, J=8.7 Hz, 1H), 6.98 (t, 1H), 6.65 (s, 2H), 6.50-6.46 (m, 1H), 6.27-6.26 (m, 1H), 4.43-4.36 (q, J=7.2 Hz, 2H), 1.35 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-305bd947cae04948b2d628e5c68757ab
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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