Water → 1-(6-Hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

HRID 597203Notes

Reaction equation

HRID 597203 reaction equation
Br.[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.[C:13]([O-])(=[O:15])[CH3:14].[Na+].C(OC(=O)C)(=O)C.O>C(Cl)Cl>[C:13]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([OH:2])[CH:4]=2)[CH2:9]1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 133617991,2,3,4-Tetrahydroisoquinolin-6-ol--hydrogen bromide (1/1)

Product 1

HCID 133618081-(6-Hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-oneYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 57.6 g of 1,2,3,4-tetrahydro-6-hydroxy-isoquinoline-hydrobromide, 22.6 g of anhydrous sodium acetate, and 76.6 g of acetic acid anhydride in 300 ml of methylene chloride is held at the boiling point for one hour under reflux. 300 ml of water are added thereto, the organic phase is separated, and the aqueous phase is extracted several times with methylene chloride. After evaporation of the methylene chloride extract, the residue is dissolved in dilute sodium hydroxide, stirred for 30 minutes on a boiling water bath, and the reaction product is precipitated by the introduction of carbon dioxide. The filtered substance is recrystallized from ethanol. 43.5 g of 2-acetyl-1,2,3,4-tetrahydro-6-hydroxy-isoquinoline are obtained. m.p. = 135° - 136° C. (ethanol - diisopropyl ether).

Workup

  1. temperatureunder reflux
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted several times with methylene chloride
  4. customAfter evaporation of the methylene chloride
  5. extractionextract
  6. dissolutionthe residue is dissolved in dilute sodium hydroxide
  7. customthe reaction product is precipitated by the introduction of carbon dioxide
  8. customThe filtered substance is recrystallized from ethanol

Sources & evidence

ORD record
ord-f69c45c9edc2416c9eb512d015633bd0
Source dataset
uspto-grants-1977_03
Patent number
US04013663

Reaction notes

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