Sodium Hydroxide → 3-(1-Ethoxy-1-phenylmethylidene)-5-nitro-2-indolinone

HRID 1637920Notes

Reaction equation

HRID 1637920 reaction equation
[OH-].[Na+].C([N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[C:8](=[C:18]([O:25][CH2:26][CH3:27])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]1=[O:28])(=O)C>C(Cl)Cl.CCO>[CH2:26]([O:25][C:18](=[C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[NH:6][C:7]1=[O:28])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:27]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 542801041-Acetyl-3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone

Product 1

HCID 537348873-(1-Ethoxy-1-phenylmethylidene)-5-nitro-2-indolinone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 equivalents of 1N sodium hydroxide solution are added dropwise to a stirred mixture of 1-acetyl-3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone in methylene chloride (11 ml/g) and EtOH (8.5 ml/g) whilst cooling with ice so that the internal temperature does not exceed 14 to 17° C. Then stirring is continued for 0.5 hours at ambient temperature and the methylene chloride is eliminated by evaporation in vacuo at a bath temperature of 30° C. Water is added (11 ml/g) and the mixture is thoroughly stirred. The precipitate is filtered, washed with water, isopropanol and lastly with ether and dried at 100° C.

Workup

  1. temperaturewhilst cooling with ice so that the internal temperature
  2. customdoes not exceed 14 to 17° C
  3. customthe methylene chloride is eliminated by evaporation in vacuo at a bath temperature of 30° C
  4. additionWater is added (11 ml/g)
  5. stirringthe mixture is thoroughly stirred
  6. filtrationThe precipitate is filtered
  7. washwashed with water, isopropanol and lastly with ether
  8. customdried at 100° C.

Sources & evidence

ORD record
ord-56741eaa769148658b15db5bed1e62d1
Source dataset
uspto-grants-2000_03
Patent number
US06043254

Reaction notes

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