Acetone → HCID 21183738, compound

HRID 1384807Notes

Reaction equation

HRID 1384807 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14]CC)=O)=[C:5]2[C:17](=O)[C:18]([O:20][CH3:21])=[O:19].[C:23]1([NH:29][NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O.CC(C)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12](=[O:14])[N:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:30]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 7516PhenylhydrazineHCID 21183734HCID 21183734, compound

Product 1

HCID 21183738HCID 21183738, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 19 g (59 mmol) of methyl 5-chloro-2-(ethoxycarbonyl)-1-methyl-α-oxo-1H-indole-3-acetate and 26 g (240 mmol) of phenylhydrazine in 250 ml of acetic acid is heated at reflux for 2 h. The mixture is cooled, 250 ml of a 1/1 mixture of water and of acetone are added and the mixture is left standing at 4° C. for 15 h. The precipitate is collected by filtration, washed with water and with acetone and dried under reduced pressure. 17.4 g (47 mmol) of solid are obtained.

Workup

  1. temperatureat reflux for 2 h
  2. temperatureThe mixture is cooled
  3. waitthe mixture is left
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with water and with acetone
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-82dfafd9a6014fcb8e33407994cefb58
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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