E-ethyl 5-(2-(dimethylamino)vinyl)-2,4-dinitrobenzoate → Ethyl 6-amino-1H-indole-5-carboxylate

HRID 1908502Notes

Reaction equation

HRID 1908502 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[C:6]([N+:19]([O-])=O)=[CH:7][C:8]([N+:16]([O-])=O)=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H][H]>[Ni].CCO>[NH2:16][C:8]1[CH:7]=[C:6]2[C:5]([CH:4]=[CH:3][NH:19]2)=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 10590973E-ethyl 5-(2-(dimethylamino)vinyl)-2,4-dinitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of (E)-ethyl 5-(2-(dimethylamino)vinyl)-2,4-dinitrobenzoate (15 g, 0.050 mol) and Raney Nickel (5 g) in EtOH (500 mL) was hydrogenated at room temperature under 50 psi of hydrogen 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-5-carboxylate (3.0 g, 30%). 1H NMR (DMSO-d6) δ 10.68 (s, 1H), 7.99 (s, 1H), 7.01-7.06 (m, 1H), 6.62 (s, 1H), 6.27-6.28 (m, 1H), 6.16 (s, 2H), 4.22 (q, J=7.2 Hz, 2H), 1.32-1.27 (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 on silica gel

Sources & evidence

ORD record
ord-4c0f5e7b4f064a1f82966b900b4a3e2b
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

Loading…