HCID 85979144, compound → HCID 14567254, compound

HRID 443382Notes

Reaction equation

HRID 443382 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[C:10]([C:11]=1[CH:12]=[N:13]O)=[CH:9][CH:8]=[CH:7][CH:6]=2>N.[Ni]>[NH2:13][CH2:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:3][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 85979144HCID 85979144, compound

Product 1

HCID 14567254HCID 14567254, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

12.5 g 3-Chloro-1-phenyl-isoquinoline-4-aldoxime are hydrogenated in 500 ml of methanolic ammonia in the presence of 30 g of prehydrogenated Raney-nickel, at room temperature and under atmospheric pressure. After 30 minutes, the precipitate is filtered off from the catalyst, the solution is concentrated and the residue is chromatographed on 200 g of silica gel using a mixture of chloroform and methanol (8:2). 2.5 g 4-Aminomethyl-3-chloro-1-phenyl-isoquinoline having a melting point from 101° to 103° C. are isolated.

Workup

  1. filtrationthe precipitate is filtered off from the catalyst
  2. concentrationthe solution is concentrated
  3. customthe residue is chromatographed on 200 g of silica gel using
  4. additiona mixture of chloroform and methanol (8:2)

Sources & evidence

ORD record
ord-2502d2638fa04bd682ddc3bf84eaa439
Source dataset
uspto-grants-1981_04
Patent number
US04260611

Reaction notes

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