Hydrochloric Acid → 6-(4-Methylphenyl)-2-methylquinoline-3-carboxylic acid

HRID 1387962Notes

Reaction equation

HRID 1387962 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[C:13]([CH3:18])[C:12]([C:19]([O:21]C)=[O:20])=[CH:11]3)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1CCO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[C:13]([CH3:18])[C:12]([C:19]([OH:21])=[O:20])=[CH:11]3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18472437Methyl 6-(4-methylphenyl)-2-methylquinoline-3-carboxylate

Product 1

HCID 229902036-(4-Methylphenyl)-2-methylquinoline-3-carboxylic acidYield 68.8%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

To a solution of methyl 6-(4-methylphenyl)-2-methylquinoline-3-carboxylate (0.99 g) in tetrahydrofuran-ethanol (5-5 ml) was added 2N sodium hydroxide (2 ml) at room temperature, and the mixture was stirred for 2 days. To the reaction mixture was added 1N hydrochloric acid (4 ml), and the mixture was concentrated under reduced pressure to precipitate crystals, which were collected by filtration and washed with ethanol and diethylether to give 6-(4-methylphenyl)-2-methylquinoline-3-carboxylic acid (648 mg) as colorless crystals.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto precipitate crystals, which
  3. filtrationwere collected by filtration
  4. washwashed with ethanol and diethylether

Sources & evidence

ORD record
ord-e38390a3567b45328be01dc0f31f5809
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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