5-(2-Dimethylamino-vinyl)-2,4-dinitro-benzoic acid ethyl ester → Ethyl 6-amino-1H-indole-5-carboxylate

HRID 423784Notes

Reaction equation

HRID 423784 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[C:9]([CH:11]=[CH:12]N(C)C)[C:8]([N+:16]([O-])=O)=[CH:7][C:6]=1[N+:19]([O-])=O)[CH3:2]>CCO.[Ni]>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][C:6]=1[NH2:19])[NH:16][CH:12]=[CH:11]2)=[O:22])[CH3:2]

Participants

4

Reactant 1

HCID 851972815-(2-Dimethylamino-vinyl)-2,4-dinitro-benzoic acid ethyl ester

Product 1

HCID 10726870Ethyl 6-amino-1H-indole-5-carboxylateYield 30%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-(2-dimethylamino-vinyl)-2,4-dinitro-benzoic acid ethyl ester (15 g, 0.05 mol) and Raney Ni (5 g) in EtOH (500 mL) was stirred under H2 (50 psi) at room temperature 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-5-carboxylic acid ethyl ester (B-25) (3 g, 30%). 1H NMR (DMSO-d6) δ 10.68 (s, 1 H), 7.99 (s, 1 H), 7.01-7.06 (m, 1 H), 6.62 (s, 1 H), 6.27-6.28 (m, 1 H), 6.16 (s, 2 H), 4.22 (q,J=7.2 Hz, 2 H), 1.32-1.27 (t,J=7.2 Hz, 3 H).

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-c001198fa01f44d7be2715b8297306b8
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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