Trifluoroacetic anhydride → 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbonitrile

Temperatur

0 °C

To a cold solution of 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxamide (7.2 g, 47.3 mmol, Journal of Organic Chemistry, 1959, 24, 196) in DCM (70 mL) was added TEA (13.19 mL, 95 mmol) and TFAA (8.02 mL, 56.8 mmol) at about 0° C. The reaction mixture was stirred for about 2 h at about 0° C. The reaction mixture was filtered and the filtrate was diluted with DCM (100 mL). The organic layer was washed successively with water (2×70 mL) and brine (1×70 mL). The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford 1-methyl-2-oxo-1,2-dihydropyridine-4-carbonitrile as a white solid 3.3 g, (52.0%), 1H NMR (400 MHz, DMSO) δ: 7.94-7.92 (d, J=7.2 Hz, 1H), 7.00 (s, 1H), 6.53-6.50 (dd, J=2 Hz, 1 Hz), 3.45 (s, 3H), LC/MS (Table 1, Method d) Rt=0.77 min.

1. filtrationThe reaction mixture was filtered
2. additionthe filtrate was diluted with DCM (100 mL)
3. washThe organic layer was washed successively with water (2×70 mL) and brine (1×70 mL)
4. dry with materialThe organic layer was dried over sodium sulphate
5. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-fb7a249dc8874c5dbc65259abcb6c09f

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09029409B2