Nitric Acid → HCID 21877762、化合物

HRID 1922460ノート

反応式

HRID 1922460 の反応式
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])=[O:5].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O.O>[F:13][C:8]1[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=[C:12]2[C:7]=1[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

参加物

5

反応物 2

HCID 944Nitric AcidHCID 42560293-chloro-N-(2-fluorophenyl)propanamide

生成物 1

HCID 21877762HCID 21877762、化合物収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
-5 °C

実験手順

To a stirred solution of 8-fluoro-3,4-dihydroquinolin-2(1H)-one (see Example 41 for details) (2 g, 12.11 mmol) in sulfuric acid (12 ml), cooled to −5° C. was added nitric acid, 90% (0.565 ml, 12.11 mmol) as a 1:1 solution in water. The reaction mixture was stirred at −5° C. for 20 min, then quenched via addition of ice, precipitating the product which was collected by filtration. The pale solid was then dissolved in dichloromethane, dried, filtered and concentrated, and then chromatographed on silica gel using 0-10% ethyl acetate in dichloromethane as eluent to give the desired 8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (2.33 g, 11.09 mmol, 92% yield). 1H NMR (DMSO-d6) δ 10.73 (brs, 1H), 8.03 (m, 1H), 8.02 (m, 1H), 3.08 (t, J=7.5 Hz, 2H), 2.57 (t, J=7.5 Hz, 1H).

後処理

  1. customquenched via addition of ice
  2. customprecipitating the product which
  3. filtrationwas collected by filtration
  4. dissolutionThe pale solid was then dissolved in dichloromethane
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel using 0-10% ethyl acetate in dichloromethane as eluent

出典と根拠

ORDレコード
ord-ffa6994d787a4ccbbece8dbac04ee105
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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