Methanol → 3-Chloro-6-fluoro-1-methoxyisoquinoline

Reaction equation

[Na].Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[CH:6]=[C:5]([Cl:14])[N:4]=1.[CH3:15][OH:16]>>[Cl:14][C:5]1[N:4]=[C:3]([O:16][CH3:15])[C:12]2[C:7]([CH:6]=1)=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2

Participants

Reactant 3

HCID 887Methanol

HCID 5360545Sodium

HCID 468399601,3-Dichloro-6-fluoroisoquinoline

Product 1

HCID 866882843-Chloro-6-fluoro-1-methoxyisoquinoline

Conditions

Temperature: 70 °C

Procedure

To a solution of 125 mg (3.00 mmol) sodium in 40 mL MeOH was added 668 mg (3.00 mmol) 1,3-dichloro-6-fluoro-isoquinoline. The reaction mixture was stirred at 70° C. for 30 min. The solvent was removed by distillation and the residue diluted with ice water. The precipitate was filtered off, washed with water and dried.