Acetyl chloride → N-[2-(6-Methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl]acetamide

HRID 17859Notes

Reaction equation

HRID 17859 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([O:21][CH3:22])=[CH:10][CH:9]=2.C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>ClCCl>[CH3:22][O:21][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:23])[N:6]([CH3:24])[C:5]([CH2:4][CH2:3][NH:2][C:32](=[O:34])[CH3:33])=[C:14]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 684337913-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride

Product 1

HCID 11382522N-[2-(6-Methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-aminoethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one hydrochloride (75 mg, 0.22 mmol) in 2 mL of dichloromethane was added triethylamine (0.076 mL, 0.54 mmol), followed by acetyl chloride (0.017 mL, 0.24 mmol). After 45 minutes, the mixture was partitioned between EtOAc and 10% citric acid solution, and the organic layer was washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC to provide the titled product as a colorless oil. Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C21H22N2O3 (M+H+): 351.1703. Found 351.1681.

Workup

  1. customthe mixture was partitioned between EtOAc and 10% citric acid solution
  2. washthe organic layer was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-295d840c58324a119d932037e4966130
Source dataset
uspto-grants-2010_06
Patent number
US07741322B2

Reaction notes

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