Sulfuric Acid → 2-methylquinoline-7-carboxylic Acid

HRID 338859

Reaction equation

HRID 338859 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12](F)(F)F)=[CH:7][CH:8]=2)[N:3]=1.[OH:16]S(O)(=O)=O.[OH-:21].[Na+]>>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([OH:16])=[O:21])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 224169042-Methyl-7-(trifluoromethyl)quinoline

Product 1

HCID 109762212-methylquinoline-7-carboxylic AcidYield 71.6%

Conditions

Temperature
230 °C

Procedure

A mixture of 2-methyl-7-(trifluoromethyl)quinoline (5.2 g, 24.6 mmol) and 80% H2SO4 (18.1 g, 148 mmol) was heated at 230° C. for 20 minutes. After cooling to ambient temperature, the mixture was basified by 6 N NaOH to about pH 12. The resulting solid was removed by filtration. The filtrate was acidified by 2 N HCl to about pH 3, extracted with 3:1 DCM/IPA (2×50 mL), dried (sodium sulfate), filtered and concentrated under reduced pressure to give 2-methylquinoline-7-carboxylic acid (3.3 g, 71.6%) as a solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customThe resulting solid was removed by filtration
  3. extractionextracted with 3:1 DCM/IPA (2×50 mL)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c376a21c9d04023ac37545bbdbe6036
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Linked notes

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