Hydrochloric Acid → 4-(2-Chlorophenyl)-6,8-dimethyl-2-quinolinecarboxylic acid

HRID 1656442Notes

Reaction equation

HRID 1656442 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[C:13]([CH3:19])[CH:14]=[C:15]([CH3:18])[CH:16]=2)[N:11]=[CH:10][C:9]=1C#N.[OH-:22].[Na+].COC[CH2:27][OH:28].Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[C:13]([CH3:19])[CH:14]=[C:15]([CH3:18])[CH:16]=2)[N:11]=[C:10]([C:27]([OH:28])=[O:22])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 103796024-(2-Chlorophenyl)-6,8-dimethyl-3-quinolinecarbonitrile

Product 1

HCID 197880374-(2-Chlorophenyl)-6,8-dimethyl-2-quinolinecarboxylic acidYield 86.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(2-chlorophenyl)-6,8-dimethyl-3-quinolinecarbonitrile (0.5 g), 6N-sodium hydroxide (1.5 ml) and 2-methoxyethanol (3 ml) was refluxed under stirring for 8 hrs. The mixture was diluted with water and acidified with hydrochloric acid. The resultant precipitate was collected by filtration to give 4-(2-chlorophenyl)-6,8-dimethyl-2-quinolinecarboxylic acid (0.46 g, 86.8%), which was recrystallized from ethanol to give colorless prisms. m.p. 234°-235° C. This substance was identical with that obtained in Reference Example 33.

Workup

  1. temperaturewas refluxed
  2. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-b0d23f09576f4425a79fbc06803b29f0
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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