Isopropenyl acetate → 2-Acetyl-8-amino-7-chloro-1,2,3,4-tetrahydroisoquinoline

HRID 1288460Notes

Reaction equation

HRID 1288460 reaction equation
[NH2:1][C:2]1[C:3]([Cl:12])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][NH:9][CH2:8][CH2:7]2.[C:13](OC(C)=C)(=[O:15])[CH3:14]>C(OCC)(=O)C>[C:13]([N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([NH2:1])[C:3]([Cl:12])=[CH:4][CH:5]=2)[CH2:10]1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7916Isopropenyl acetateHCID 213938238-Amino-7-chloro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 205232142-Acetyl-8-amino-7-chloro-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8-Amino-7-chloro-1,2,3,4-tetrahydroisoquinoline, prepared as in Example 12, is treated with one molar equivalent of isopropenyl acetate in refluxing ethyl acetate for 16 hours. The solvent is evaporated and the residue crystallized from benzene to yield 2-acetyl-8-amino-7-chloro-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. customThe solvent is evaporated
  2. customthe residue crystallized from benzene

Sources & evidence

ORD record
ord-4c610062b31c45648b73fcaecd3ceab1
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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