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

HRID 1726974Notes

Reaction equation

HRID 1726974 reaction equation
Cl.CN(C)[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[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:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=2)=[N:25][C:23]=1[CH3:24]

Participants

4

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 690367913-(Dimethylamino)-1-(3-(trifluoromethyl)phenyl)propan-1-one hydrochloride

Product 1

HCID 690396242-Methyl-6-(3-trifluoromethyl-phenyl)-nicotinic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.57 g (19.76 mmol) of the above prepared 3-dimethylamino-1-(3-trifluoromethyl-phenyl)-propan-1-one hydrochloride and 2.28 g (1.00 eq.) of 3-aminocrotonic acid methyl ester were dissolved in 60 ml of AcOH and heated to reflux for 4 h. After cooling, the bulk of the solvent was evaporated i. V., 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=89/11) delivered finally 2.00 g of the title compound as light yellow crystals of mp. 47-49° C. (dec.).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. temperatureAfter cooling
  4. customthe bulk of the solvent was evaporated i
  5. dissolution, the 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=89/11)

Sources & evidence

ORD record
ord-f1a8862a6fae4e57abbb1788d5ecc66b
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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