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

HRID 461482Notes

Reaction equation

HRID 461482 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-0759dc88c64547519de640fc840752a1
Source dataset
uspto-grants-1977_12
Patent number
US04062961

Reaction notes

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