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

HRID 1823814ノート

反応式

HRID 1823814 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 101082523-Chloromethylsulfonyl-7-fluoro-1-methyl-4-quinolone収率 77.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1858e462a07942c786955f18a9ee48f0
出典データセット
uspto-grants-2006_05
特許番号
US07041677B2

反応ノート

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