Water → 7-Hydroxy-3,4-dihydro-2H-isoquinolin-1-one

HRID 1750085Notes

Reaction equation

HRID 1750085 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][NH:13][C:14]2=[O:17])=[CH:9][CH:8]=1.O.CCOC(C)=O>C(Cl)Cl>[OH:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][NH:13][C:14]2=[O:17])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 135216727-Methoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 442032017-Hydroxy-3,4-dihydro-2H-isoquinolin-1-oneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (4.75 mL, 47.5 mmol, in CH2Cl2) was added to a cold solution (ice-bath) of intermediate 18 (3.36 g, 18.98 mmol) in CH2Cl2 (100 mL). The mixture was then warmed to rt and stirred overnight. Water was carefully added dropwise to quench the reaction. EtOAc was added and the mixture was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated to afford 7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (intermediate 19) (2.46 g, 80%) as a white solid. mp: 201-203° C.

Workup

  1. customto quench
  2. customthe reaction
  3. washthe mixture was washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-77bbc28285814192a0a7c4e5daf37607
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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