Dimethylamine → 6-(Dimethylamino)-1,2-dihydroisoquinolin-1-one

HRID 2069743

Reaction equation

HRID 2069743 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2.[CH3:13][NH:14][CH3:15]>C(O)C>[CH3:13][N:14]([CH3:15])[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 674DimethylamineHCID 450908026-Fluoroisoquinolin-1(2H)-one

Product 1

HCID 574241426-(Dimethylamino)-1,2-dihydroisoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

6-Fluoro-2H-isoquinolin-1-one (54 mg, 0.33 mmol) was deposited in a sealed tube with 5 mL 33% dimethylamine in ethanol. This was heated at 150° C. for 3.5 hours. This was concentrated in vacuo and purified by flash chromatography (gradient elution 50 to 100% ethyl acetate/hexanes) to yield 6-Dimethylamino-2H-isoquinolin-1-one (39 mg, 0.21 mmol). MS (ESI) 189.1 (M+H)−.

Workup

  1. concentrationThis was concentrated in vacuo
  2. custompurified by flash chromatography (gradient elution 50 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-45bdd3b449d544b8801d551331c06025
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Linked notes

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