Boron tribromide → 6-hydroxyisoquinolin-1(2H)-one

HRID 1621297Notes

Reaction equation

HRID 1621297 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH:7]=[CH:6]2.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 218898546-methoxyisoquinolin-1(2H)-one

Product 1

HCID 105111706-hydroxyisoquinolin-1(2H)-oneYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.54 g of 6-Methoxy-2H-isoquinolin-1-one (65) were dissolved in 50 mL of dry dichloromethane and at 0° C. 2.74 mL of boron tribromide were carefully added. The mixture was allowed to stir at room temperature for 18 h and was then poured on ice/water. The organic layer was separated, washed with brine, dried over sodium sulphate and evaporated to dryness. The crude material was purified by silica gel chromatography to yield 1.96 g of the desired product.

Workup

  1. additionwas then poured on ice/water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness
  6. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ec9abe89fc6b45c48096bd0f95e15658
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Reaction notes

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