Hydrochloric Acid → 6-Methyl-2-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid

HRID 423241Notes

Reaction equation

HRID 423241 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.[OH-].[Na+].O.Cl>CO>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:18])[F:20])=[CH:13][CH:12]=2)[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 586297476-Methyl-2-(4-trifluoromethylphenyl)nicotinic acid methyl ester

Product 1

HCID 299877526-Methyl-2-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

6-Methyl-2-(4-trifluoromethyl-phenyl)nicotinic acid methyl ester (7.26 g) was dissolved in methanol (30 mL). 4M sodium hydroxide (7.2 mL) was added thereto at 0° C. under cooling. The mixture was stirred at 45° C. for 3 hours. Water (30 mL) was added to the mixture at 0° C. under cooling, followed by acidification (pH=3) with 1M hydrochloric acid (about 30 mL) to give the precipitate. The precipitate was filtered and dried to give the title compound as a colorless solid (6.5 g). 1H-NMR (δ, 300 MHz, CDCl3): 2.66 (3H, s), 7.61 (2H, d, J=8.3 Hz), 7.67 (2H, d, J=8.3 Hz), 7.27 (1H, d, J=7.9 Hz), 8.18 (1H, d, J=7.9 Hz)

Workup

  1. temperatureunder cooling
  2. customto give the precipitate
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-d3d24ee53ef144c8807cd4d9a6d584ae
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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