Hydrochloric Acid → 4-(2-Methylpyridin-4-yl)benzoic acid

HRID 379564Notes

Reaction equation

HRID 379564 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].O.Cl>CO>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22329711Ethyl 4-(2-methyl-4-pyridyl)benzoate

Product 1

HCID 186177484-(2-Methylpyridin-4-yl)benzoic acidYield 44.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-(2-methyl-4-pyridyl)benzoate (185 mg) was dissolved in methanol (7.5 ml) and 1.0M NaOH (3.75 ml) and heated at 60° C. for 3 hours. The resulting mixture was reduced to low volume then water (10 ml) added, the solution neutralised to pH 7 with 10M HCl, the resulting precipitate filtered and dried over P2O5 to give 4-(2-methyl-4-pyridyl)benzoic acid as a light brown solid (73 mg); mp 293-294° C.; 1H NMR (300 MHz, DMSO-d6) δ=2.52 (s,3H), 7.53 (d,1H), 7.62 (s,1H), 7.89 (d,2H), 8.04 (d,2H), 8.52 (d1H) ppm. MS: m/z 214 (M+H)+.

Workup

  1. filtrationthe resulting precipitate filtered
  2. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-6a5f57f8344c4cdbbf8611fed387716f
Source dataset
uspto-grants-2001_10
Patent number
US06300330B1

Reaction notes

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