m-Chloroperbenzoic acid → 3-Chloromethylsulfonyl-7-fluoro-1-methyl-4-quinolone

HRID 1581769

반응식

HRID 1581769 반응식
[Cl:1][CH2:2][S:3]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([F:16])=[CH:11][CH:12]=2)[N:7]([CH3:17])[CH:6]=1)=[O:4].ClC1C=C(C=CC=1)C(OO)=[O:23]>C(Cl)Cl>[Cl:1][CH2:2][S:3]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([F:16])=[CH:11][CH:12]=2)[N:7]([CH3:17])[CH:6]=1)(=[O:23])=[O:4]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 104685473-Chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone

생성물 1

HCID 101082523-Chloromethylsulfonyl-7-fluoro-1-methyl-4-quinolone수율 77.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

6.33 g (0.0232 mole) of monochloroflosequinan (4) and 225 ml of methylene dichloride were placed in a 500 ml round bottom flask and stirred. Into this mixture a 5.98 g of 77% pure m-chloroperoxybenzoic acid (8) was added in four equal portions in 15 minute intervals and the mixture was stirred for an additional 30 minutes to complete oxidation. The reaction mixture was then concentrated to a final volume of 100 ml and the crystals which formed were filtered off and washed with two 10 ml portions of methylene dichloride. After high vacuum drying 5.2 g (77.6% yield) of white crystalline 3-chloromethylsulfonyl-7-fluoro-1-methyl-4-quinolone (9) were collected. The product was 99+% pure (by 1H NMR). 1H NMR, CDCl3, δ=8.52 dd, 1H, J=6.3 & 9.0 Hz, H at C5; 8.41 s, 1H, H at C2; 7.20 dd, 1H, J=2.1 & 9.6 Hz, H at C8; 7.32-7.26 m, 1H, H at C6; 5.03 s, 2H, CH2; 3.94 s, 3H, N—CH3.

후처리

  1. stirringthe mixture was stirred for an additional 30 minutes
  2. concentrationThe reaction mixture was then concentrated to a final volume of 100 ml
  3. customthe crystals which formed
  4. filtrationwere filtered off
  5. washwashed with two 10 ml portions of methylene dichloride

출처 및 근거

ORD 기록
ord-bcf1ff0b08f74bc88d6d319221187850
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06730790B2

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