Methyl 3-aminocrotonate → 2-Methyl-6-(4-trifluoromethyl-phenyl)-nicotinic Acid Methyl Ester

HRID 890434Notes

Reaction equation

HRID 890434 reaction equation
Cl.CN(C)[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)=O.[CH3:19][O:20][C:21](=[O:26])/[CH:22]=[C:23](\[NH2:25])/[CH3:24]>CC(O)=O>[CH3:19][O:20][C:21](=[O:26])[C:22]1[CH:4]=[CH:5][C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=2)=[N:25][C:23]=1[CH3:24]

Participants

4

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 21935704HCID 21935704, compound

Product 1

HCID 670722692-Methyl-6-(4-trifluoromethyl-phenyl)-nicotinic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.59 g (16.3 mmol) of the above prepared 3-dimethylamino-1-(4-trifluoromethyl-phenyl)-propan-1-one hydrochloride and 1.86 g (1.0 eq.) of 3-aminocrotonic acid methyl ester were dissolved in 50 ml of AcOH and heated to reflux for 4 h. After cooling, the bulk of the solvent was evaporated in vacuum, the residue dissolved in AcOEt, and washed with water and brine. Drying over sodium sulfate, evaporation of the solvents and flash chromatography (SiO2, hexane/AcOEt=8/2) delivered finally 2.40 g of the title compound as light yellow waxy solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. temperatureAfter cooling
  4. customthe bulk of the solvent was evaporated in vacuum
  5. dissolutionthe residue dissolved in AcOEt
  6. washwashed with water and brine
  7. dry with materialDrying over sodium sulfate, evaporation of the solvents and flash chromatography (SiO2, hexane/AcOEt=8/2)

Sources & evidence

ORD record
ord-307c38f77aec4220828a32b3f0290b8d
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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