Water → HCID 18976201, compound

HRID 2393623Notes

Reaction equation

HRID 2393623 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:12][CH:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[N:15]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:14]1=[O:31].O>CS(C)=O>[NH2:12][C:13]1([CH2:3][CH2:2][C:1]#[N:4])[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[N:15]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:14]1=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 7855AcrylonitrileHCID 11430Potassium CarbonateHCID 18976159HCID 18976159, compound

Product 1

HCID 18976201HCID 18976201, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under argon atmosphere, 1.2 ml of acrylonitrile and 4.48 g of potassium carbonate were added to a stirred suspension of 5.00 g of 3-amino-1-(4-fluorophenyl)-2,3-dihydro-6-methoxy-1H-indol-2-one hydrochloride in dimethyl sulfoxide (30 ml), and the mixture was stirred at room temperature for 9 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the extract was washed, dried and then filtered, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform-ethyl acetate (1:1)] to afford 3.48 g of 3-[3-amino-1-(4-fluorophenyl)-2,3-dihydro-6-methoxy-2-oxo-1H-indol-3-yl]propanonitrile as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the extract was washed
  3. customdried
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [chloroform-ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-431c7f6652764286bb00c2df3ebb88fb
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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