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

HRID 1522572노트

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HRID 1522572 반응식
[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

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 674695392-(3-Fluoro-6-methylpyridin-2-yl)-5-methylpyridine 1-oxide

생성물 1

HCID 674695932-(3-Fluoro-6-methylpyridin-2-yl)-5-methyl-4-nitropyridine 1-oxide

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8ba6658c81b04306b6c8b5c3b3624fb4
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073918B2

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