1-Methyl-5-nitroindolin-2-one → 5-Amino-1-methyl-2-oxoindoline

HRID 1887716Notes

Reaction equation

HRID 1887716 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:14]>CO>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[C:3](=[O:14])[CH2:4]2

Participants

3

Reactant 1

HCID 27279611-Methyl-5-nitroindolin-2-one

Product 1

HCID 226924705-Amino-1-methyl-2-oxoindoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-methyl-5-nitroindolin-2-one (92 mg, 0.48 mmol) in 20 mL MeOH, was Pd(C) (9.2 mg, 10 weight %) added. The round bottom flask was capped with a rubber septum and put under a hydrogen atmosphere. After 18 h the hydrogen gas was evacuated by introducing argon to the round bottom flask. The reaction mixture was filtered through celite. The celite was washed with EtOAc (2×30 ml). The volatiles were evaporated to afford the title compound in quantitative yield.

Workup

  1. additionadded
  2. customThe round bottom flask was capped with a rubber septum
  3. customAfter 18 h the hydrogen gas was evacuated
  4. additionby introducing argon to the round bottom flask
  5. filtrationThe reaction mixture was filtered through celite
  6. washThe celite was washed with EtOAc (2×30 ml)
  7. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-b5eb5aec81774aafb1f4c668139b86ef
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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