Pyridine → HCID 57558094, compound

HRID 1162933Notes

Reaction equation

HRID 1162933 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[Cl:23][CH2:24][C:25](Cl)=[O:26].N1C=CC=CC=1>C1C=CC=CC=1>[Cl:23][CH2:24][C:25]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:20])[F:21])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1)=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 231567387-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 57558094HCID 57558094, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (100 mg, 0.329 mmol) obtained in step C of Example 1-1 was dissolved in benzene (2 ml). Thereafter, chloroacetic acid chloride (29 μl, 0.362 mmol) and pyridine (80 μl, 0.986 mmol) were added to the solution, and the obtained mixture was stirred at a room temperature for 4 hours. Thereafter, the reaction solution was washed with 1 N hydrochloric acid, and was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was suspended in and washed with cold ethyl acetate, and a solid was collected by filtration, so as to obtain 2-chloro-N-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]acetamide (70 mg, 56%).

Workup

  1. washThereafter, the reaction solution was washed with 1 N hydrochloric acid
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. washwashed with cold ethyl acetate
  6. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-1741c9ba40fa409ead71c96dcc25356c
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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