Isopropenyl acetate → 1-(7-Amino-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

HRID 2059014Notes

Reaction equation

HRID 2059014 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][CH:3]=1.[C:12](OC(C)=C)(=[O:14])[CH3:13]>C(OCC)(=O)C>[C:12]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH2:9]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7916Isopropenyl acetateHCID 115863231,2,3,4-Tetrahydroisoquinolin-7-amine

Product 1

HCID 128113521-(7-Amino-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.5 g. (16.8 mmol) 7-amino-1,2,3,4-tetrahydroisoquinoline, 30 ml. ethyl acetate and 2 ml. isopropenyl acetate was refluxed for approximately 16 hours and was then concentrated to dryness at reduced pressure. The residue was then recrystallized from a mixture of ethyl acetate and petroleum ether to afford 2-acetyl-7-amino-1,2,3,4-tetrahydroisoquinoline with a melting point of 98°-100° C.

Workup

  1. additionA mixture of 2.5 g
  2. concentrationwas then concentrated to dryness at reduced pressure
  3. customThe residue was then recrystallized from a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-85e629680283409ea9fc1a6d928d5202
Source dataset
uspto-grants-1982_03
Patent number
US04321254

Reaction notes

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