1-Isoquinolinamine → STK019752

HRID 1446809Notes

Reaction equation

HRID 1446809 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:12]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:17]=[CH:16][C:15]([CH:18]([C:20](C(Br)C2C=CC(C3C=CC=CC=3)=CC=2)=O)Br)=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[C:12]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:13]=[CH:14][C:15]([C:18]2[N:1]=[C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[CH:4][N:3]3[CH:20]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 737421-IsoquinolinamineHCID 86737811HCID 86737811, compound

Product 1

HCID 1338745STK019752

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4.32 g. (0.03 mole) of 1-amino-isoquinoline and 8.25 g. (0.03 mole) of [(1,1'-biphenyl)-4-yl]-bromomethyl-ketone in 100 ml. of chloroform was heated on a boiling water bath for about 10 minutes until a precipitate separated. The solvent was distilled off at atmospheric pressure and the residue was heated under vacuum for 30 minutes at 100° C. It was subsequently taken up with 50 ml of water and the resulting solution was made alkaline by means of 70 ml. of aqueous 10% sodium hydroxide. After extracting with 500 ml. of methylene chloride and evaporating the solvent, a residue was obtained which was re-crystallized from ethylene glycol monomethylether. Yield 3.0 g. M.p. 221°-22° C.

Workup

  1. customseparated
  2. distillationThe solvent was distilled off at atmospheric pressure
  3. extractionAfter extracting with 500 ml
  4. customof methylene chloride and evaporating the solvent
  5. customa residue was obtained which
  6. customwas re-crystallized from ethylene glycol monomethylether

Sources & evidence

ORD record
ord-9b94ea4a78b34cc6afbf3ba2be2499b5
Source dataset
uspto-grants-1982_02
Patent number
US04313950

Reaction notes

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