Hydrochloric Acid → 4-(4-Phenylbenzyl)quinoline-6-carboxylic acid

HRID 1699808Notes

Reaction equation

HRID 1699808 reaction equation
CC1(C)C[O:5][C:4]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=N1.Cl.[OH-:32].[Na+]>C(O)C>[C:24]1([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][C:10]3[C:9]4[C:14](=[CH:15][CH:16]=[C:7]([C:4]([OH:5])=[O:32])[CH:8]=4)[N:13]=[CH:12][CH:11]=3)=[CH:23][CH:22]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 22388009HCID 22388009, compound

Product 1

HCID 223882954-(4-Phenylbenzyl)quinoline-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(4,5-dihydro-4,4-dimethyloxazol-2-yl)-4-(4-phenylbenzyl)-quinoline (132 mg), ethanol (1 ml) and 3N hydrochloric acid (3 ml) was refluxed under heating for 2 hr. Then 6N hydrochloric acid (3 ml) was added and the mixtured was refluxed for 4 hr. The mixture was basified with aqueous sodium hydroxide solution, and washed once with chloroform. The aqueous layer was adjusted to pH 4 with 1N hydrochloric acid. The resulting precipitate was collected by filtration and washed with water to give the objective compound (87 mg) as a white powder.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 2 hr
  3. temperaturethe mixtured was refluxed for 4 hr
  4. washwashed once with chloroform
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-4f7b23a4fad045bf97127715125bdc03
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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