Ethyl Acetate → 1-(5-amino-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

HRID 1194101

Reaction equation

HRID 1194101 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH2:7]2.[C:12](OCC)(=[O:14])[CH3:13]>>[C:12]([N:6]1[CH2:5][CH2:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH2:1])[CH2:7]1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 162174995-Amino-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 212717261-(5-amino-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

Procedure

A stirred mixture of 5-amino-1,2,3,4-tetrahydroisoquinoline (10.0 g) isopropenyl acetate (7.2 g) and ethyl acetate (150 ml) was heated under reflux for 24 hours. The cooled, filtered solution was evaporated under reduced pressure to a small volume. The residual oil was purified by elution from a silica column with ethyl acetate/methanol mixtures followed by crystallisation from ethyl acetate to give 2-acetyl-5-amino-1,2,3,4-tetrahydroisoquinoline as a white solid 6.6 g, m.p. 107°-108° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. filtrationThe cooled, filtered solution
  4. customwas evaporated under reduced pressure to a small volume
  5. customThe residual oil was purified by elution from a silica column with ethyl acetate/methanol
  6. custommixtures followed by crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-a7dac60dbebf4db894de4bc2f0cbd37e
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Linked notes

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