Acetic Acid → 5-amino-3,3-dimethylindolin-2-one

HRID 1088946Notes

Reaction equation

HRID 1088946 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH2:7]2)([O-])=O.[CH3:14][OH:15].[C:16](O)(=O)C>[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:14](=[O:15])[C:7]2([CH3:16])[CH3:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 2303665-Nitro-2-oxindole

Product 1

HCID 221620915-amino-3,3-dimethylindolin-2-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
40 °C

Procedure

A suspension of 100 g. (0.48 mol) 5-nitroindolin-2-one in 2500 ml. methanol with 200 ml. glacial acetic acid is hydrogenated, while stirring well, at 40° C. in the presence of 10 g. of 10% Pd/C. The subsequently clear solution is freed from catalyst by suction filtration and the filtrate is evaporated. Yield: 82 g. (96% of theory); m.p. 185°-191° C. (HCl-salt from methanol).

Workup

  1. additionA suspension of 100 g
  2. filtrationThe subsequently clear solution is freed from catalyst by suction filtration
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-60e5b4ec92d4426ab0e94aea81529e76
Source dataset
uspto-grants-1990_10
Patent number
US04963686

Reaction notes

Loading…