HCID 10614807, compound → Ethyl 6-amino-1H-indole-7-carboxylate

HRID 2038029Notes

Reaction equation

HRID 2038029 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[C:6]([N+:19]([O-])=O)=[C:7]([C:13]([N+:16]([O-])=O)=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]>[Ni].CCO>[NH2:16][C:13]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]2[C:5]([CH:4]=[CH:3][NH:19]2)=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 10614807HCID 10614807, compound

Product 1

HCID 10822051Ethyl 6-amino-1H-indole-7-carboxylateYield 16.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of (E)-ethyl 3-(2-(dimethylamino)vinyl)-2,6-dinitrobenzoate (30 g, 0.097 mol) and Raney Nickel (10 g) in EtOH (1000 mL) was hydrogenated at room temperature under 50 psi for 2 h. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was purified by column on silica gel to give ethyl 6-amino-1H-indole-7-carboxylate as an off-white solid (3.2 g, 16%). 1 H NMR (DMSO-d6) δ 10.38(s, 1 H), 7.42(d, i=8.7 Hz, 1 H), 6.98(t, J=3.0 Hz, 1 H), 6.65(s, 2 H), 6.48(d, J=8.7 Hz, 1 H), 6.27-6.26(m, 1 H), 4.38 q, 7.2 Hz, 2 H), 1.35(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 on silica gel

Sources & evidence

ORD record
ord-423c35f1999c4081866049ee4b493d40
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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