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

HRID 1384964Notes

Reaction equation

HRID 1384964 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-0f94edde94c54f98b14b7ac69a9e744a
Source dataset
uspto-grants-2001_07
Patent number
US06262068B1

Reaction notes

Loading…