Sodium Carbonate → 2-(3-Fluoro-6-methylpyridin-2-yl)-5-methyl-4-nitropyridine 1-oxide

HRID 1522572Notes

Reaction equation

[F:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N+:10]=2[O-:16])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[N+:17]([O-])([O-:19])=[O:18].[K+].C([O-])([O-])=O.[Na+].[Na+]>OS(O)(=O)=O>[F:1][C:2]1[C:3]([C:9]2[CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:12]([CH3:15])=[CH:11][N+:10]=2[O-:16])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of cold H2SO4 (0-10° C.) (170 mL) was added 2-(3-fluoro-6-methylpyridin-2-yl)-5-methylpyridine 1-oxide (4. g, 19. mmol) followed by portionwise addition of KNO3 (4 g, 39 mmol) and the reaction was heated overnight at 80° C. The reaction mixture was then cooled to room temperature, and poured into ice-water and the pH adjusted to about 8 with a saturated solution of Na2CO3. The mixture was extracted with dichloromethane, the organic layer dried, and purified by flash silica chromatography eluted with petroleum ether/ethyl acetate (4:1) to give 2-(3-fluoro-6-methylpyridin-2-yl)-5-methyl-4-nitropyridine 1-oxide. (2.9 g; 57.8%). 1HNMR (CDCL3): δ ppm 8.37 (s, 1H), 8.27 (s, 1H), 7.50-7.47 (m, 1H), 7.38-7.37 (m, 1H), 2.70 (s, 3H), 2.64 (s, 3H).

Workup

temperatureThe reaction mixture was then cooled to room temperature
extractionThe mixture was extracted with dichloromethane
customthe organic layer dried
custompurified by flash silica chromatography
washeluted with petroleum ether/ethyl acetate (4:1)

Sources & evidence

ORD record: ord-8ba6658c81b04306b6c8b5c3b3624fb4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073918B2

Reaction notes

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