Acetyl chloride → Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

HRID 432595Notes

Reaction equation

HRID 432595 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]([OH:14])=[O:13])[NH:7][CH2:6][CH2:5]2.[C:15](Cl)(=O)C>CO>[CH3:15][O:13][C:12]([CH:8]1[C:9]2[C:4](=[CH:3][C:2]([OH:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][NH:7]1)=[O:14]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 5904306-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Product 1

HCID 2759854Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 1,2,3,4-tetrahydro-6-hydroxy-1-isoquinolinecarboxylic acid (5.0 g, 25.9 mmol, prepared according to W. K. Anderson, H. L. McPherson, J. S. New and A. C. Rick, Journal of Medicinal Chemistry, Vol. 27, p. 1321, 1984) in methanol (150 mL) was treated with acetyl chloride (3 mL) (reaction mixture became homogenous) and heated under reflux for 24 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo. It was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution and water. After drying over anhydrous magnesium sulfate, the solvent was removed in vacuo to yield the title compound (4.0 g, 75%) as a colorless solid, mp 214-216° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. additionIt was diluted with ethyl acetate
  5. washwashed with saturated sodium bicarbonate solution and water
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f151b1bbd45745b7a530cca52c7e3fc9
Source dataset
uspto-grants-2003_12
Patent number
US06664250B2

Reaction notes

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