Chloroform → 1-Phenylisoquinoline-4-carboxylic acid

HRID 652728Notes

Reaction equation

HRID 652728 reaction equation
C(Cl)(Cl)Cl.[C:5]([O:8]CC)(=[O:7])[CH3:6].C(C1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:15][CH:14]=1)#N.[OH-].[Na+]>C(O)(=O)C>[C:23]1([C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]([C:5]([OH:8])=[O:7])=[CH:14][N:15]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 133022824-Cyano-1-phenylisoquinoline

Product 1

HCID 133022561-Phenylisoquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

20.5 g of 1-phenylisoquinoline are dissolved in 100 ml of carbon tetrachloride, and 16 g of bromine are added at room temperature. The temperature is raised slowly and the mixture is kept under reflux for 1 hour. 7.9 g of pyridine in 10 ml of carbon tetrachloride are added dropwise to the boiling reaction mixture in the course of 2 hours, and the mixture is then heated at reflux temperature for a further 18 hours. The reaction solution is decanted off from the resinous precipitate and is concentrated, and the residue is crystallized from diisopropyl ether. 11.7 g of 4-bromo-1-phenylisoquinoline of melting point 123°-125° C. are obtained. 0.7 g of 4-bromo-1-phenylisoquinoline, 0.45 g of copper cyanide and 10 ml of dimethylformamide are heated at 160° C. for 6 hours. The reaction solution is decanted off, diluted with methylene chloride and washed with water. 0.75 g of crude product are isolated from the methylene chloride phase, and 0.2 g of 4-cyano-1-phenylisoquinoline of melting point 138°-140° is obtained from this crude product by column chromatography over silica gel using a 98:2 mixture of chloroform and ethyl acetate. 0.2 g of 4-cyano-1-phenylisoquinoline is heated with 10 ml of 20% strength sodium hydroxide solution at 100° C. for 4 hours. The solution is cooled and acidified with acetic acid. The precipitate is filtered off and dried. 0.18 g of 1-phenylisoquinoline-4-carboxylic acid of melting point 215°-217° is isolated.

Workup

  1. temperatureThe solution is cooled
  2. filtrationThe precipitate is filtered off
  3. customdried

Sources & evidence

ORD record
ord-292411e3bf3446cc92ed16cb5dcb1b39
Source dataset
uspto-grants-1987_06
Patent number
US04673682

Reaction notes

Loading…