Water → HCID 54033837, compound

HRID 1973689Notes

Reaction equation

HRID 1973689 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][C:25]#[N:26].O>CN(C)C=O.C1(C)C=CC=CC=1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:22][CH2:23][CH2:24][C:25]#[N:26])[C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 214124-BromobutyronitrileHCID 24758Sodium hydrideHCID 21490326HCID 21490326, compound

Product 1

HCID 54033837HCID 54033837, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Procedure

3-(m-Chlorophenyl)-3-hydroxy-2-indolinone (31.2g) in dry dimethylformamide (120 ml.) was added dropwise with stirring under nitrogen to a suspension of sodium hydride (5.2g of a 60% dispersion in oil) in dry dimethylformamide (120ml.) while keeping the temperature at 10°C. The reaction was then left stirring at room temperature for 1 hour. 4-Bromobutyronitrile (18.6g.) in dry toluene (120 ml.) was added dropwise and the mixture stirred for 36 hours. The reaction mixture was poured into water and extracted with toluene. The organic extracts were dried over magnesium sulphate and evaporated to an oil which afforded 21.3 g. colourless crystals, m.p. 124°-126°C, from ethanol.

Workup

  1. customat 10°C
  2. waitThe reaction was then left
  3. stirringthe mixture stirred for 36 hours
  4. extractionextracted with toluene
  5. dry with materialThe organic extracts were dried over magnesium sulphate
  6. customevaporated to an oil which
  7. customafforded 21.3 g

Sources & evidence

ORD record
ord-5474415cdd9f46f2a093308bf60a6b9a
Source dataset
uspto-grants-1976_12
Patent number
US03998842

Reaction notes

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