Chloroacetyl chloride → HCID 23156812, compound

HRID 1098295Notes

Reaction equation

HRID 1098295 reaction equation
C(N(CC)CC)C.[Cl:8][CH2:9][C:10](Cl)=[O:11].[NH2:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:20][C:21]2=[O:24])=[CH:16][CH:15]=1>Cl>[Cl:8][CH2:9][C:10]([NH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[C:19]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:20][C:21]2=[O:24])=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 23156743HCID 23156743, compound

Product 1

HCID 23156812HCID 23156812, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

0.236 ml (1.69 mmol) of triethylamine and 0.101 ml (1.27 mmol) of chloroacetyl chloride were added in this order to 200 mg (0.85 mmol) of 7-amino-3-phenyl-2H-isoquinolin-1-one obtained in Example 39. The obtained mixture was stirred at a room temperature for 2 hours. Thereafter, 30 ml of 1 N hydrochloric acid was added to the reaction solution, and the mixture was then extracted with methylene chloride (30 ml×2). The extract was dried over anhydrous magnesium sulfate, and the solvent was then distilled away under reduced pressure. The precipitated solid was collected by filtration, and the filtrate was then washed with a suitable amount of ether, so as to obtain 229 mg (86%) of 2-chloro-N-(1-oxo-3-phenyl-1,2-dihydroisoquinolin-7-yl)acetamide in the form of a light brown solid.

Workup

  1. extractionthe mixture was then extracted with methylene chloride (30 ml×2)
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was then distilled away under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration
  5. washthe filtrate was then washed with a suitable amount of ether

Sources & evidence

ORD record
ord-37990939d81a4613838e7fa5843b3d4f
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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