Water → 8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 577474Notes

Reaction equation

HRID 577474 reaction equation
[Cl:1][C:2]1[C:3]([O:13]C)=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH2:8][CH2:7]2.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([OH:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 867237008-chloro-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 867237018-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-oneYield 902.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 8-chloro-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (1d, 7.8 g, 3.7 mmol) in dry CH2Cl2 (120 mL) was added dropwise BBr3 (11 mL, 111 mmol). After the addition, the mixture was stirred at room temperature overnight. To the reaction mixture was added dropwise H2O (200 mL). The mixture was extracted with EtOAc (8×200 mL), dried over Na2SO4 and concentrated under vacuum. To the residue was added EtOAc (20 mL) and petroleum ether (40 mL). The mixture was filtered and the solids were dried under vacuum to give 8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (1e, 6.6 g, 91%) as a brown solid.

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted with EtOAc (8×200 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. additionTo the residue was added EtOAc (20 mL) and petroleum ether (40 mL)
  6. filtrationThe mixture was filtered
  7. customthe solids were dried under vacuum

Sources & evidence

ORD record
ord-fc6a747341fd48dcb7ca9f40c780b479
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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