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

HRID 461486Notes

Reaction equation

HRID 461486 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-de93d36a985c4b60b933a631fc339d5c
Source dataset
uspto-grants-1977_12
Patent number
US04062961

Reaction notes

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