Ethanol → 5-amino-6-chloro-2,3-dihydro-1H-indol-2-one
Reaction equation
C(O)C.[Cl-].[NH4+].[O:6]=[C:7]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([Cl:19])=[C:12]([N+:16]([O-])=O)[CH:13]=2)[NH:8]1>[Fe].O>[O:6]=[C:7]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([Cl:19])=[C:12]([NH2:16])[CH:13]=2)[NH:8]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of ethanol (200 ml) and water (40 ml) were added ammonium chloride (2.2 g) and iron metal (19.7 g). To the mixture was added 2-oxo-5-nitro-6-chloroindoline (12.5 g) at 60° C. After refluxing for 45 minutes, the reaction mixture was filtered under warm condition. The filter cake was washed with ethanol. The combined filtrate and washings were evaporated to dryness under reduced pressure to give 2-oxo-5-amino-6-chloroindoline (10.0 g).
Workup
- temperatureAfter refluxing for 45 minutes
- filtrationthe reaction mixture was filtered
- temperatureunder warm condition
- washThe filter cake was washed with ethanol
- customThe combined filtrate and washings were evaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-4d6217ddccf543cb955d7d0b60f2f2e1
- Source dataset
- uspto-grants-1983_01
- Patent number
- US04370340
Reaction notes
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