Hydrogen Peroxide → 6-Fluoro-3-methyl-quinoline 1-oxide

HRID 1424260

反応式

HRID 1424260 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH3:12])=[CH:5]2.OO.[O-:15]S([O-])=O.[Na+].[Na+].[I-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N+:8]([O-:15])=[CH:7][C:6]([CH3:12])=[CH:5]2

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 5238Sodium IodideHCID 24437Sodium SulfiteHCID 157236166-Fluoro-3-methylquinoline2 回

生成物 1

HCID 867188376-Fluoro-3-methyl-quinoline 1-oxide

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

6-Fluoro-3-methyl-quinoline (Intermediate 28) (48.0 mg, 0.298 mmol) was dissolved in acetic acid (1 mL) and 30% aqueous H2O2 (0.040 mL, 0.396 mmol) was added. This was stirred at 80° C. for 16 h before cooling. A few mLs of a 10% aq. solution of Na2SO3 was added followed by a spatula tip of sodium iodide. This was stirred for 10 min before partitioning between ethyl acetate and sat. NaHCO3. The separated aqueous layer was extracted with ethyl acetate and the combined organics dried over MgSO4. Purification by silica gel flash chromatography (methanol/ethyl acetate) gave 6-fluoro-3-methyl-quinoline 1-oxide (29.4 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.72 (dd, J=9.4, 5.3 Hz, 1H) 8.38 (s, 1H) 7.36-7.50 (m, 3H) 2.46 (s, 3H); MS (M+1): 178.1.

後処理

  1. temperaturebefore cooling
  2. stirringThis was stirred for 10 min
  3. custombefore partitioning between ethyl acetate and sat. NaHCO3
  4. extractionThe separated aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organics dried over MgSO4
  6. customPurification by silica gel flash chromatography (methanol/ethyl acetate)

出典と根拠

ORDレコード
ord-f968d62001054602818ab34a112e710a
出典データセット
uspto-grants-2015_01
特許番号
US08927577B2

関連ノート

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