Methanol → 1-chloro-2H-isoquinolin-6-one
Reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12]C)=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.B(Br)(Br)Br.CO>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 1-chloro-6-methoxy-isoquinoline (2 g, 10.3 mmol) in DCM (60 ml) was added BBr3 in (4.9 ml, 51.6 mmol) in 10 mL THF and the reaction was heated to 50° C. overnight. The reaction was cooled to 0° C. and 30 volumes of methanol was added as a quench. The solvent was removed to afford 2.87 g (>99%) of 1-chloro-isoquinolin-6-ol as a brown solid. LCMS found 180.36 [M+H]+.
Workup
- temperatureThe reaction was cooled to 0° C.
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-91f9b6afdd3f4fa88b38b4e759f6ae89
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809267B2
Reaction notes
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