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

HRID 557365Notes

Reaction equation

HRID 557365 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[C:6]([CH3:17])([CH3:16])[CH2:5]1)(=[O:3])[CH3:2]>CO>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[C:6]([CH3:17])([CH3:16])[CH2:5]1)(=[O:3])[CH3:2]

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-Acetyl-3,3-dimethyl-6-nitroindoline (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-128873630600481d8b57913bcc33ab69
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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