Acetyl chloride → HCID 49834048, compound

HRID 2045967Notes

Reaction equation

HRID 2045967 reaction equation
NC[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[NH:7][C:6]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])C.C(Cl)(=[O:31])C>ClCCl>[O:15]=[C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([O:4][CH2:3][CH2:28][CH2:27][NH:24][C:25](=[O:31])[CH3:26])=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:7]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 49834045HCID 49834045, compound

Product 1

HCID 49834048HCID 49834048, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 150 mg (0.45 mmol) of 4-(2-amino-ethoxy)-3-phenyl-2H-isoquinolin-1-one (cmpd. 1) dichloromethane (6 mL), triethylamine (190 L, 1.36 mmol) and acetyl chloride (39.3 L, 0.55 mmol) were added under argon atmosphere at 0° C. and the mixture was stirred at room temperature overnight. The reaction mixture was then washed with water, the layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, concentrated under reduced pressure and the resulting crude was purified by flash chromatography (dichloromethane:methanol, 97:3) affording 64 mg of the title compound (42%).

Workup

  1. washThe reaction mixture was then washed with water
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting crude was purified by flash chromatography (dichloromethane:methanol, 97:3)

Sources & evidence

ORD record
ord-a4ddcb48252d4c6fbf259dd21a5b489a
Source dataset
uspto-grants-2013_11
Patent number
US08592416B2

Reaction notes

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