N-methyl-2-pyrrolidone → 6-Chloro-3-nitropyridine-2-carbonitrile

Temperature

180 °C

A mixture of 2,6-dichloro-3-nitropyridine and cuprous cyanide in 1-methyl-2-pyrrolidinone was quickly heated to 180° C. and maintained at that temperature for 15 minutes with vigorous stirring. The mixture was cooled to −10° C. and the deep brown solution was poured into ice water (3.5 L) and stirred for 30 min. The flocculent brown precipitate was collected and washed with H2O. After drying for about 1.5 h, the moist solid was extracted with boiling toluene (3×300 mL). The combined toluene extracts were washed with H2O, brine, and dried (MgSO4), concentrated. The crude product was crystallized from EtOAc/hexane to afford the title compound: mp 115-117° C.; 1H NMR(DMSO-d6) δ8.16 (dd, 1H, J=8.7, 3.0 Hz), 8.82 (d, 1H, J=9.0 Hz); MS (EI) m/z 183/185 (M+H)+; Anal Calc. For C6H2ClN3O2: C, 39.26; H, 1.10; N, 22.89. Found: C, 39.47; H, 1.38; N, 22.77.

1. temperaturemaintained at that temperature for 15 minutes with vigorous stirring
2. temperatureThe mixture was cooled to −10° C.
3. customThe flocculent brown precipitate was collected
4. washwashed with H2O
5. customAfter drying for about 1.5 h
6. extractionthe moist solid was extracted with boiling toluene (3×300 mL)
7. washThe combined toluene extracts were washed with H2O, brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated
10. customThe crude product was crystallized from EtOAc/hexane

ORD record

ord-ece5733828da4062aad601fec1c81f87

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369056B1