Hydrochloric Acid → HCID 13910344, compound

HRID 542590Notes

Reaction equation

HRID 542590 reaction equation
[C:1]([NH:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:21])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].Cl>CN(C)C=O.CN(C1C=CN=CC=1)C>[C:1]([NH:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]([C:22](=[O:24])[CH3:23])[C:13]1=[O:21])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 13910502HCID 13910502, compound

Product 1

HCID 13910344HCID 13910344, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred slurry of 841 mg (3.0 mmole) of N-benzoyl-2-oxindole-1-carboxamide in 5 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 dropwise. Stirring was continued for 1 hour, and then the reaction mixture was poured onto a mixture of 65-70 ml. of ice-water and 2.2 ml of 3N hydrochloric acid. The solid which precipitated was recovered by filtration. It was recrystallized from ethanol to give 385 mg of the title compound as tan crystals, mp 198° C.

Workup

  1. waitwas continued for a few minutes
  2. temperaturethe slurry was cooled in an ice-bath
  3. stirringStirring
  4. additionthe reaction mixture was poured onto a mixture of 65-70 ml
  5. customThe solid which precipitated
  6. filtrationwas recovered by filtration
  7. customIt was recrystallized from ethanol

Sources & evidence

ORD record
ord-837fbe49c3d64bc79a665d06bd946390
Source dataset
uspto-grants-1987_04
Patent number
US04658037

Reaction notes

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