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

HRID 2413501Notes

Reaction equation

HRID 2413501 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH2:6][CH2:5]2.[C:12](OC(=O)C)(=[O:14])[CH3:13].C(Cl)(=O)C.C(N(CC)CC)C>>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12](=[O:14])[CH3:13])[CH2:6][CH2:5]2

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 266981,2,3,4-Tetrahydroisoquinolin-6-olHCID 86587039Acetylchloride triethylamine

Product 1

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

Procedure

5.0 g of 6-hydroxy-1,2,3,4-tetrahydroisoquinoline are converted into the bisacetyl compound using acetic anhydride or acetyl chloride/triethylamine, and, without purification, this compound is heated under reflux for 6 hours with 10 ml of diethylamine in 50 ml of ethanol. The mixture is evaporated in vacuo in a rotary evaporator, and the residue is chromatographed on silica gel using ethyl acetate/methanol in the ratio 9:1. A yellow oil which crystallizes on trituration with diethyl ether is obtained. Yield: 5.2 g (78% of theory), melting point: 129°-130°.

Workup

  1. customwithout purification
  2. temperaturethis compound is heated
  3. temperatureunder reflux for 6 hours with 10 ml of diethylamine in 50 ml of ethanol
  4. customThe mixture is evaporated in vacuo in a rotary evaporator
  5. customthe residue is chromatographed on silica gel
  6. customA yellow oil which crystallizes on trituration with diethyl ether
  7. customis obtained

Sources & evidence

ORD record
ord-911048b6b4374ac99d1cc9f19e52e818
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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