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

HRID 24807Notes

Reaction equation

HRID 24807 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[C:6](=[C:16]([O:23][CH2:24][CH3:25])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]1=[O:26])(=O)C.[OH-].[Na+]>ClCCl.C(O)C>[CH2:24]([O:23][C:16](=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)[NH:4][C:5]1=[O:26])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH3:25]

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

17.6 g (50 mmol) of 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-nitro-2-indolinone are suspended in 200 ml of dichloromethane and 150 ml of ethanol. 75 ml of 1N sodium hydroxide solution are added at 0° C. and the mixture is then stirred for another 30 minutes at ambient temperature. The reaction solution is evaporated down by half and 200 ml of water are then added. The product precipitated is suction filtered, washed with water, isopropanol and ether and dried.

Workup

  1. customThe reaction solution is evaporated down by half and 200 ml of water
  2. additionare then added
  3. customThe product precipitated
  4. filtrationfiltered
  5. washwashed with water, isopropanol and ether
  6. customdried

Sources & evidence

ORD record
ord-79444c592f9f4e44b1df26a7b6fdd8e8
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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