Ethanol → 77859-59-7

HRID 1164523Notes

Reaction equation

HRID 1164523 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]1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 18932798HCID 18932798, compound

Product 1

HCID 2046666477859-59-7Yield 93.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

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

  1. temperatureAfter refluxing for 45 minutes
  2. filtrationthe reaction mixture was filtered
  3. temperatureunder warm condition
  4. washThe filter cake was washed with ethanol
  5. 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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