ChemicalBook CAS DataBase List 4-(TRIFLUOROMETHYL)NICOTINAMIDE

4-(TRIFLUOROMETHYL)NICOTINAMIDE synthesis

8synthesis methods

Product Name:4-(TRIFLUOROMETHYL)NICOTINAMIDE
CAS Number:158062-71-6
Molecular formula:C7H5F3N2O
Molecular Weight:190.12

2-Propenenitrile, 3-[(4,4,4-trifluoro-3-oxo-1-buten-1-yl)amino]-, (2Z)-

533932-97-7

2-Propenenitrile, 3-[(4,4,4-trifluoro-3-oxo-1-buten-1-yl)amino]-, (2E)-

533932-96-6

158062-71-6

Sodium hydroxide (600 mg, 15 mmol) was added as 3-[(4,4,4-trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (mixture of IIa and IIb, 1.90 g, 10 mmol) and methanol (15 mL). The reaction mixture was heated to reflux for 6 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with hexane/acetone (1:1, v/v) as eluent to afford 4-(trifluoromethyl)nicotinamide (1.25 g, 65.6% yield). The product was characterized by 1H-NMR (200 MHz, DMSO-d6): δ 8.89 (1H, d, J = 5.1 Hz), 8.82 (1H, s), 8.18 (1H, brs), 7.85 (1H, brs), 7.81 (1H, d, J = 5.1 Hz).

533932-97-7
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533932-96-6
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158062-71-6
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Yield:158062-71-6 65.6%

Reaction Conditions:

with sodium hydroxide in methanol for 6 h;Heating / reflux;

Steps:

8 Reference Example 8; 4-Trifluoromethylnicotinamide (Compound VIIc, Step F)
(Reference Example 8) 4-Trifluoromethylnicotinamide (Compound VIIc, Step F) 3-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (a mixture of IIa and IIb; 1.90g, 10 mmol) was dissolved in methanol (15 ml), and sodium hydroxide (600 mg, 15 mmol) was added.. The mixture was heated under reflux for 6 hours.. The reaction mixture was concentrated under reduced pressure.. The resulting residue was purified by silica gel column chromatography (a eluding solvent: hexane/acetone =1/1) to obtain 1.25 g (yield 65.6%) of the title compound.1H-NMR spectrum (200 MHz, DMSO-d6) δ (ppm) 8.89 (1H, d, J=5.1Hz), 8.82 (1H, s), 8.18 (1H, brs), 7.85 (1H, brs), 7.81 (1H, d, J=5.1Hz).

References:

Sankyo Agro Company, Limited EP1460071, 2004, A1 Location in patent:Page 39

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158063-67-3 Synthesis