Water → 3-Methyl-1,2-dihydroisoquinolin-1-one

HRID 1713394Notes

Reaction equation

HRID 1713394 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][C:3]=1[CH3:13].O>I>[CH3:13][C:3]1[NH:4][C:5](=[O:12])[C:6]2[C:11]([CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 962WaterHCID 2245674-hydroxy-3-methyl-2H-isoquinolin-1-one

Product 1

HCID 32444773-Methyl-1,2-dihydroisoquinolin-1-oneYield 46%

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

24.6 g (140 mmol) of 4-hydroxy-3-methyl-2H-isoquinolin-1-one are heated together with 9.13 g (294 mmol) of red phosphorus in 55% hydriodic acid (130 ml) at 160° C. for 7 days. The cooled mixture is poured into water and extracted with dichloromethane. 10.2 g (46% yield) of a white solid are obtained.

Workup

  1. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-c6fe089fc4034bf78dbfc9309990ef97
Source dataset
uspto-grants-2010_09
Patent number
US07795278B2

Reaction notes

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