5-Chloro-6,7-dimethoxy-3,4-dihydroisoquinolin-1(2H)-one → 5-Chloro-6,7-dihydroxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 525846Notes

Reaction equation

HRID 525846 reaction equation
[Cl:1][C:2]1[C:11]([O:12]C)=[C:10]([O:14]C)[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:16]>ClCCl.CO>[Cl:1][C:2]1[C:11]([OH:12])=[C:10]([OH:14])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:16]

Participants

4

Reactant 1

HCID 642812755-Chloro-6,7-dimethoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 717439535-Chloro-6,7-dihydroxy-3,4-dihydroisoquinolin-1(2H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of 5-chloro-6,7-dimethoxy-3,4-dihydroisoquinolin-1(2H)-one (700 mg, 2.90 mmol) in dichloromethane (DCM) (2 mL) at −78° C. was added borontribromide (0.821 mL, 8.69 mmol). Mixture was allowed to warm up to room temperature and stirred at room temperature for 1 hour. Mixture was diluted with methanol and stripped several times to give 5-chloro-6,7-dihydroxy-3,4-dihydroisoquinolin-1(2H)-one (619 mg, 2.90 mmol, 100% yield) LCMS (M+H)+: 214.0

Sources & evidence

ORD record
ord-6bdd8537f9ac48fa89861cf8ed491da9
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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