Acetic Acid → 8-Isoquinolinamine,7-chloro-(9CI)

HRID 1288456Notes

Reaction equation

HRID 1288456 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.C(O)(=O)C.C(O)C.[OH-].[NH4+]>[Zn].O>[NH2:12][C:11]1[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[CH:9]=[N:8][CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14923Ammonium HydroxideHCID 13051702HCID 13051702, compound

Product 1

HCID 213938438-Isoquinolinamine,7-chloro-(9CI)

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A mixture of 9.5 g. of 7-chloro-8-nitroisoquinoline, and 14.4 g. of zinc and 48 ml. of acetic acid in 450 ml. of ethanol and 70 ml. of water is heated on a steam bath for five minutes. The reaction mixture is cooled, made alkaline with aqueous ammonium hydroxide and extracted with ethyl acetate. The ethyl acetate is removed from the extract in vacuo to give, as the residue, 8-amino-7-chloroisoquinoline.

Workup

  1. additionA mixture of 9.5 g
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate is removed from the
  5. extractionextract in vacuo

Sources & evidence

ORD record
ord-267af5854d5746d9a6f24777fe130867
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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