Hydrochloric Acid → 3-Quinolinecarboxylic acid, 6-chloro-4-phenyl-

HRID 1656437Notes

Reaction equation

HRID 1656437 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14]CC)=[O:13])=[C:5]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[K+].C(O)C.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([OH:14])=[O:13])=[C:5]2[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 1486468HCID 1486468, compound

Product 1

HCID 103791113-Quinolinecarboxylic acid, 6-chloro-4-phenyl-Yield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 6-chloro-4-phenyl-3-quinolinecarboxylate (2.5 g), potassium hydroxide (2.24 g) and ethanol (25 ml) was heated for 10 mins. at 80° C. The mixture was diluted with water and acidified with hydrochloric acid to give 6-chloro-4-phenyl-3-quinolinecarboxylic acid as crystals (2.20 g, 96.9%), which was recrystallized from a mixture of methanol and chloroform as pale yellow prisms. m.p. 269°-270° C.

Workup

  1. temperaturewas heated for 10 mins
  2. customat 80° C

Sources & evidence

ORD record
ord-3b00192a47a143fc9260d7206c65789c
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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