Hydrochloric Acid → 2-Methoxy-6-(trifluoromethyl)nicotinic acid

HRID 1865477Notes

Reaction equation

HRID 1865477 reaction equation
Cl[C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:15][O-:16].[Na+].O.Cl>CO>[CH3:15][O:16][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acidHCID 10942334Sodium Methoxide

Product 1

HCID 686830352-Methoxy-6-(trifluoromethyl)nicotinic acidYield 55.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-chloro-6-(trifluoromethyl)nicotinic acid (2 g, 8.9 mmol) and sodium methoxide (1.9 g, 36 mmol) in methanol (20 mL) was heated at reflux for 48 hours. The mixture was allowed to cool to room temperature then poured into water (50 mL). This was cooled in an ice-bath and acidified with hydrochloric acid (2 N, aq). The resulting precipitate was filtered and dried to give 2-methoxy-6-(trifluoromethyl)nicotinic acid as a white solid (1.1 g): 1H NMR (400 MHz, CDCl3): δ 8.61 (1H, d, J 7.7), 7.48 (1H, d, J 7.7), 4.25 (3H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. temperatureThis was cooled in an ice-bath
  4. filtrationThe resulting precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-58b46a339fa44d1382cc02d9b1cb2a27
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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