Benzoyl chloride → N-[2-(2-Dimethylamino-ethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-benzamide

HRID 1037764Notes

Reaction equation

HRID 1037764 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:7]2=[O:12].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:16][N:15]([CH3:17])[CH2:14][CH2:13][N:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]1=[O:12]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 595794535-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one

Product 1

HCID 24785069N-[2-(2-Dimethylamino-ethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one (50 mg, 0.0002 mol), benzoyl chloride (36 mg, 0.00026 mol) and N,N-diisopropylethylamine (110 mg, 0.00086 mol) were stirred in methylene chloride (3 mL, 0.05 mol) at room temperature for 2 hours. The mixture was diluted with CH2Cl2 (20 mL) and the organic layer was separated and washed with NaHCO3 (10 mL), dried over Na2SO4, and purified via flash column chromatography (12 g of silica gel, 10% MeOH/CH2Cl2) to give the product as a light yellow solid.

Workup

  1. customthe organic layer was separated
  2. washwashed with NaHCO3 (10 mL)
  3. dry with materialdried over Na2SO4
  4. custompurified via flash column chromatography (12 g of silica gel, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1c61e1c981894fe38d119ef3be83c2c3
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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