Hydrochloric Acid → Methyl 4-(trifluoromethyl)nicotinate

HRID 1064555

Reaction equation

HRID 1064555 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=O)[CH:4]=[CH:5][NH:6][CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10].Cl>CO>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[CH:5][N:6]=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 85078003Methyl 3-(4,4,4-trifluoro-3-oxo-1-butenylamino)acrylate

Product 1

HCID 2775680Methyl 4-(trifluoromethyl)nicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

19 g (0.1 mol) of methyl 3-(4,4,4-trifluoro-3-oxo-1-butenylamino)acrylate were dissolved in 200 ml of methanol in a three-neck flask and 1 g of Li2CO3 was added. The reaction mixture was heated for 6-8 h under reflux, cooled to 30° C. and 10 ml of aqueous HCl were added. The reaction mixture was stirred for 1 h, the methanol removed under reduced pressure and the product extracted with diethyl ether. The solvent was removed and methyl 4-trifluoronicotinate purified by vacuum distillation. 14 g (81%) of the product having a boiling point of 80° C./18 mbar were obtained.

Workup

  1. temperatureThe reaction mixture was heated for 6-8 h
  2. temperatureunder reflux
  3. customthe methanol removed under reduced pressure
  4. extractionthe product extracted with diethyl ether
  5. customThe solvent was removed
  6. distillationmethyl 4-trifluoronicotinate purified by vacuum distillation
  7. customwere obtained

Sources & evidence

ORD record
ord-bd86838e06404dffaf5a2cbe637b05d8
Source dataset
uspto-grants-2005_11
Patent number
US06969768B2

Linked notes

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