Hydrochloric Acid → HCID 13565454, compound

HRID 1589381Notes

Reaction equation

HRID 1589381 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C:12]2=[O:20])=[O:10])=[CH:4][CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].Cl>CN(C)C=O.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([C:21](=[O:23])[CH3:22])[C:12]2=[O:20])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 13565642HCID 13565642, compound

Product 1

HCID 13565454HCID 13565454, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred slurry of 811 mg (3.0 mmole) of N-(4-fluorophenyl)-2-oxindole-1-carboxamide in 4 ml of N,N-dimethylformamide was added 806 mg (6.6 mmole) of 4-(N,N-dimethylamino)pyridine. Stirring was continued for a few minutes, and then the slurry was cooled in an ice-bath and a solution of 337 mg (3.3 mmole) of acetic anhydride in 2 ml of N,N-dimethylformamide was added. Stirring was continued for 1 hour, and then the reaction mixture was poured onto a mixture of 60 ml of ice-water and 2.2 ml of 3N hydrochloric acid. The solid which precipitated was recovered by filtration. It was recrystallized from acetonitrile to give 600 mg of the title compound as dark crystals, mp 181°-182° C.

Workup

  1. waitwas continued for a few minutes
  2. temperaturethe slurry was cooled in an ice-bath
  3. stirringStirring
  4. customThe solid which precipitated
  5. filtrationwas recovered by filtration
  6. customIt was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-2c888715da54430c9493cac68de9335d
Source dataset
uspto-grants-1986_02
Patent number
US04569942

Reaction notes

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