Acetic Acid → 5-amino-3,3-dimethylindolin-2-one
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
Product 1
Reagents, catalysts & solvents 1
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
- additionA suspension of 100 g
- filtrationThe subsequently clear solution is freed from catalyst by suction filtration
- customthe filtrate is evaporated
Sources & evidence
- ORD record
- ord-c653d752dd9641c0ac16fd68af973fde
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04666923
Reaction notes
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