Methyl 4-o-tolyl-nicotinoate → 4-(2-Methylphenyl)nicotinic acid

HRID 379367Notes

Reaction equation

HRID 379367 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][N:10]=[CH:9][CH:8]=1>C(O)C.[OH-].[Na+]>[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 15887405Methyl 4-o-tolyl-nicotinoate

Product 1

HCID 158874064-(2-Methylphenyl)nicotinic acidYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.13 g (5.0 mmol) methyl 4-o-tolyl-nicotinoate in 15 ml ethanol and 12 ml 2 N sodium hydroxide solution was heated to reflux for 1 h. The pH was adjusted to 5 and the mixture was extracted twice with ethyl acetate. The combined organic layers were dried (sodium sulfate) and evaporated to give 1 g (94%) of the title compound as off white crystals.

Workup

  1. temperatureto reflux for 1 h
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried (sodium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-38a6c4874bee4b68b051a271670f5e37
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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