Nitric Acid → HCID 21877762, 화합물

HRID 1922460노트

반응식

HRID 1922460 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 21877762HCID 21877762, 화합물수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 1118Sulfuric Acid용매

반응 조건

온도
-5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ffa6994d787a4ccbbece8dbac04ee105
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173813B2

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