Water → HCID 21183743, compound

HRID 1384802Notes

Reaction equation

HRID 1384802 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:11][C:12]([C:14]1[N:15]([CH2:30][CH3:31])[C:16]2[C:21]([C:22]=1[C:23](=O)[C:24]([O:26][CH3:27])=[O:25])=[CH:20][C:19]([F:29])=[CH:18][CH:17]=2)=O)C.O>C(O)(=O)C>[CH2:30]([N:15]1[C:16]2[CH:17]=[CH:18][C:19]([F:29])=[CH:20][C:21]=2[C:22]2[C:23]([C:24]([O:26][CH3:27])=[O:25])=[N:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:12](=[O:11])[C:14]1=2)[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 7516PhenylhydrazineHCID 21183741HCID 21183741, compound

Product 1

HCID 21183743HCID 21183743, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

18.4 ml (187.2 mmol) of phenylhydrazine are added, at room temperature, to a solution of 14 g (43.6 mmol) of methyl 2-(ethoxycarbonyl)-1-ethyl-5-fluoro-α-oxo-1H-indole-3-acetate in 150 ml of acetic acid and the reaction mixture is stirred for 30 min at room temperature and then for 2 h at reflux. The mixture is cooled, 100 ml of water are added and an insoluble material is separated by filtration, the insoluble material being washed on sintered glass with a 70/30 mixture of water and acetone. 10.5 g (28.6 mmol) of white solid are thus isolated, which solid is used as is in the following stage.

Workup

  1. temperaturefor 2 h at reflux
  2. temperatureThe mixture is cooled
  3. customan insoluble material is separated by filtration
  4. washthe insoluble material being washed on sintered glass with a 70/30 mixture of water and acetone

Sources & evidence

ORD record
ord-85d06cda336a426181d76d56d2e7293e
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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