1-Phenyl-5-chloroisoquinoline → 1-Phenyl-5-cyanoisoquinoline

HRID 1156905Notes

Reaction equation

HRID 1156905 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[C:12](Cl)[CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cu](C#N)[C:19]#[N:20]>CN(P(N(C)C)(N(C)C)=O)C>[C:1]1([C:7]2[C:16]3[C:11](=[C:12]([C:19]#[N:20])[CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 128518471-Phenyl-5-chloroisoquinolineHCID 178418260HCID 178418260, compound

Product 1

HCID 205339031-Phenyl-5-cyanoisoquinoline

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

1-Amino-2-(2-chlorophenyl)ethane and benzoyl chloride were reacted in the same way as in step (a) of Example 13 to afford 1-benzoylamino-2-(2-chlorophenyl)-ethane having a melting point of 70.1° to 71.0° C. (b) 1-Benzoylamino-2-(2-chlorophenyl)ethane, phosphorus oxychloride and phosphorus pentoxide were reacted in the same way as in step (b) of Example 13 to afford 1-phenyl-5-chloro-3,4-dihydroquinoline as an oil. (c) 1-Phenyl-5-chloro-3,4-dihydroisoquinoline and diphenyl disulfide were reacted in the same way as in step (c) of Example 13 to afford 1-phenyl-5-chloroisoquinoline as colorless needles having a melting point of 66.0° to 66.6° C. (d) 1-Phenyl-5-chloroisoquinoline, copper cyanide and hexamethylphosphotriamide were reacted in the same way as in step (d) of Example 13 to afford 1-phenyl-5-cyanoisoquinoline as an oil. (e) 1-Phenyl-5-cyanoisoquinoline was treated in the same way as in step (e) of Example 13 to afford 1-phenyl-5-methoxycarbonylisoquinoline as colorless needles having a melting point of 102.2° to 103.1° C. (f) 1-Phenyl-5-methoxycarbonylisoquinoline and dihydrobis(2-methoxyethoxy)aluminum sodium (in 70% benzene) were reacted in the same way as in step (f) of Example 13 to afford 1-phenyl-5-hydroxymethylisoquinoline as colorless plates having a melting point of 97.3° to 97.9° C. (g) 1-Phenyl-5-hydroxymethylisoquinoline was treated in the same way as in step (g) of Example 13 to afford 1-phenyl-5-chloromethylisoquinoline having a melting point of 104.0° to 104.2° C. (h) 1-Phenyl-5-chloromethylisoquinoline was treated by the same way as in step (h) of Example 13 to afford 1-phenylisoquinoline-5-acetonitrile as an oil.

Workup

  1. customwere reacted in the same way as in step (d) of Example 13

Sources & evidence

ORD record
ord-3caedeaf9e6548bc842cb4b96f140dec
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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