Hydrazine → ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate

HRID 2118114Notes

Reaction equation

HRID 2118114 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:9]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C(O)C.[Ni]>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:10]2[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 69231884ethyl 1-benzyl-5-nitro-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 69229300ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylateYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A large excess of Raney® nickel was added in portions to a stirred solution of ethyl 1-benzyl-5-nitro-3-phenyl-1H-indole-2-carboxylate (1.20 g, 3 mmol) and hydrazine (1.5 mL, 47.9 mmol) in 50 mL of ethanol. After stirring at room temperature for 2 h the catalyst was then removed by filtering through a short pad of Celite®521. The filtrate was concentrated to give ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate (1.0 g, 90%) as an off-white solid: 1H NMR (DMSO-d6) δ 0.91 (t, J=7.0 Hz, 3H, 4.03 (q, J=7.0 Hz, 2H, 4.77 (s, 2H, 5.71 (s, 2H, 6.61 (d, J=1.8 Hz, 1H, 6.75 (d, J=2.2 Hz, 1H, 7.21-7.45 (m, 11H); MS (EI) m/z 371.2 (MH+).

Workup

  1. customwas then removed
  2. filtrationby filtering through a short pad of Celite®521
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f2e5b1d8edd54d15aaba0e9ac14e2179
Source dataset
uspto-grants-2008_10
Patent number
US07442805B2

Reaction notes

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