1-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone → 1-(6-Amino-3,3-dimethylindolin-1-yl)ethanone

HRID 887563Notes

Reaction equation

HRID 887563 reaction equation
[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[N:4]([C:14](=[O:16])[CH3:15])[CH2:3]1>CO>[C:14]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=2)[C:2]([CH3:17])([CH3:1])[CH2:3]1)(=[O:16])[CH3:15]

Participants

3

Reactant 1

HCID 161274181-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

Product 1

HCID 218651761-(6-Amino-3,3-dimethylindolin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3,3-Dimethyl-6-nitro-2,3-dihydro-indol-1-yl)ethanone (250 mg) was dissolved in MeOH (20 mL), the mixture was bubbled with H2 for 10 min. 10% Pd/C (50 mg) was added and the mixture was stirred under H2 overnight. The mixture was filtered through Celite® and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 1:1 EtOAc:CH2Cl2 to afford the title compound as a white crystalline material. MS: 205 (M+1). Calc'd. for C12H16N2O—204.27.

Workup

  1. customthe mixture was bubbled with H2 for 10 min
  2. addition10% Pd/C (50 mg) was added
  3. filtrationThe mixture was filtered through Celite®
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography on silica gel with 1:1 EtOAc

Sources & evidence

ORD record
ord-9ed77d0ea87f4cfdb44c2d7e231108bb
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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