Dimethylamine → 6-(Dimethylamino)-3,4-dihydroisoquinolin-1(2H)-one

HRID 2069739Notes

Reaction equation

HRID 2069739 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]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][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 674DimethylamineHCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 574241216-(Dimethylamino)-3,4-dihydroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

6-Fluoro-3,4-dihydro-2H-isoquinolin-1-one (1.56 g, 9.45 mmol) was deposited in a sealed vessel with 25 mL 33% dimethylamine in ethanol. This was heated at 150° C. for 7 hours. The resulting solution was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (elution with ethyl acetate) to yield 6-Dimethylamino-3,4-dihydro-2H-isoquinolin-1-one (787 mg, 4.14 mmol). MS (ESI) 191.1 (M+H)+.

Workup

  1. customThe resulting solution was partitioned between ethyl acetate and water
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography (elution with ethyl acetate)

Sources & evidence

ORD record
ord-967910be29b240c1a2a473050288264b
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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