Hydrochloric Acid → 5-Chloro-3-acetyl-2-oxindole-1-carboxamide

HRID 637341Notes

Reaction equation

HRID 637341 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([NH2:13])=[O:12])[C:6](=[O:14])[CH2:5]2.[C:15](OC(=O)C)(=[O:17])[CH3:16].O.Cl>CN(C1C=CN=CC=1)C.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([NH2:13])=[O:12])[C:6](=[O:14])[CH:5]2[C:15](=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide

Product 1

HCID 136474555-Chloro-3-acetyl-2-oxindole-1-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A stirred slurry of 842 mg (4.0 mmole) of 5-chloro-2-oxindole-1-carboxamide and 1.08 g (8.8 mmole) of 4-(N,N-dimethylamino)pyridine in 15 ml of N,N-dimethylformamide was cooled to ice-bath temperature, and then a solution of 449 mg (4.4 mmole) of acetic anhydride in 5 ml of N,N-dimethylformamide was added dropwise. Stirring was continued for ca. 30 minutes, and then the reaction mixture was poured into a mixture of 75 ml of water and 3 ml of 3N hydrochloric acid. The resulting mixture was cooled in an ice-bath and the solid was recovered by filtration. The solid was recrystallized from acetic acid to give 600 mg of fluffy, pale pink crystals, m.p. 237.5° C. (dec.).

Workup

  1. temperatureThe resulting mixture was cooled in an ice-bath
  2. filtrationthe solid was recovered by filtration
  3. customThe solid was recrystallized from acetic acid
  4. customto give 600 mg of fluffy, pale pink crystals, m.p. 237.5° C. (dec.)

Sources & evidence

ORD record
ord-9d3e11427ca04f5bbd27319d9993f14a
Source dataset
uspto-grants-1985_12
Patent number
US04556672

Reaction notes

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