Sodium Hydroxide → 6-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 257041Notes

Reaction equation

HRID 257041 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][CH2:7][CH2:6]2.B(Br)(Br)Br.[OH-].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 159083146-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline (31.3 g, 177 mmol) in CH2Cl2 (300 mL) at -78° is added BBr3 (33.4 mL, 353 mmol). The reaction mixture is allowed to come to ambient temperature and is stirred for 12 hours. After this time the reaction mixture is cooled to 0° and is subsequently neutralized with 5N NaOH (150 mL) solution and saturated NaHCO3 solution. The resulting precipitate is extracted with hot acetone (4×500 mL) and the combined organics are concentrated in vacuo to give 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. customto come to ambient temperature
  2. temperatureAfter this time the reaction mixture is cooled to 0°
  3. extractionThe resulting precipitate is extracted with hot acetone (4×500 mL)
  4. concentrationthe combined organics are concentrated in vacuo

Sources & evidence

ORD record
ord-cde0f9c9426944b1bad9653365145d00
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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