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

HRID 1522572ノート

反応式

HRID 1522572 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8ba6658c81b04306b6c8b5c3b3624fb4
出典データセット
uspto-grants-2015_07
特許番号
US09073918B2

反応ノート

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