8-methylisoquinolin-1(2H)-one → 8-Methyl-3,4-dihydroisoquinolin-1(2H)-one

HRID 577511Notes

Reaction equation

HRID 577511 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH:8]=[CH:7]2>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 3552438-methylisoquinolin-1(2H)-one

Product 1

HCID 533993508-Methyl-3,4-dihydroisoquinolin-1(2H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8-methylisoquinolin-1(2H)-one (76a, 1 g, 6.29 mmol) and 10% Pd/C (0.5 g) in MeOH (20 mL) was hydrogenated under H2 (60 psi) at 80° C. for 48 hours. The reaction mixture was filtered and the solids were washed with MeOH (2×20 mL). The filtrate was concentrated under vacuum to give 8-methyl-3,4-dihydroisoquinolin-1(2H)-one (76b, 1 g, ˜100%) as a gray solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with MeOH (2×20 mL)
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3e4eac214edd48f6b4f68c6c14de38db
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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