Acrylonitrile → HCID 18976158, compound

HRID 2393614Notes

Reaction equation

HRID 2393614 reaction equation
Cl.[NH2:2][CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:4]1=[O:21].C(=O)([O-])[O-].[K+].[K+].[C:28](#[N:31])[CH:29]=[CH2:30]>CS(C)=O>[NH2:2][C:3]1([CH2:30][CH2:29][C:28]#[N:31])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:4]1=[O:21]

Participants

5

Reactant 3

HCID 7855Acrylonitrile2×HCID 11430Potassium CarbonateHCID 18976174HCID 18976174, compound

Product 1

HCID 18976158HCID 18976158, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 60 g of 3-amino-1-(4-fluorophenyl)-2,3-dihydro-5-methoxy-1H-indol-2-one hydrochloride, 43 g of potassium carbonate, 20 ml of acrylonitrile and 200 ml of dimethyl sulfoxide was stirred at room temperature under argon atmosphere for 2 hours. 2 ml of acrylonitrile was added to the mixture, and stirring was continued overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered, the filtrate was concentrated under reduced pressure. Precipitated crystals were collected by filtration to afford 46.8 g of 3-[3-amino-1-(4-fluorophenyl)-2,3-dihydro-5-methoxy-2-oxo-1H-indol-3-yl]propanenitrile. Melting point 136° to 138° C. EI-MS (m/z): 325 (M+).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customPrecipitated crystals
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-69654bb98c8142379aef082ebb063356
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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