m-Chloroperbenzoic acid → Methyl 6-methylnicotinate 1-oxide

HRID 14207

반응식

HRID 14207 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N+:3]=1[O-:20]

참가 물질

5

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 231548Methyl 6-methylnicotinate

생성물 1

HCID 15883477Methyl 6-methylnicotinate 1-oxide수율 92.8%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 6-methylnicotinate (6.05 g) in methylene chloride (100 mL) was added m-chloroperbenzoic acid (77%, 13.5 g). The reaction mixture was stirred at room temperature for 2 h and then diluted with chloroform (100 mL). The mixture was washed successively with aqueous sodium sulfite, saturated sodium bicarbonate, and brine. The organic later was then dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide 6.21 g of methyl 6-methylnicotinate 1-oxide. A solution of methyl 6-methylnicotinate 1-oxide (4.35 g) in acetic anhydride (50 mL) was heated at 120° C. for 2 h and then concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 1:2 to 3:5 ethyl acetate/hexanes) provided 3.3 g of the title compound: 3H NMR (300 MHz, CDCl3) δ 9.18, 8.31, 7.44, 5.29, 3.96, 2.19.

후처리

  1. washThe mixture was washed successively with aqueous sodium sulfite, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic later was then dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-40dc59b8757c438b9eb3b2a6028290ff
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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