Ethyl 2-(3-fluoro-2-nitrophenyl)acetate → 7-Fluoro-2,3-dihydro-1h-indol-2-one

HRID 661108

반응식

HRID 661108 반응식
[F:1][C:2]1[C:3]([N+:14]([O-])=O)=[C:4]([CH2:8][C:9](OCC)=[O:10])[CH:5]=[CH:6][CH:7]=1>[Fe].CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:14][C:9](=[O:10])[CH2:8]2

참가 물질

4

반응물 1

HCID 57931102Ethyl 2-(3-fluoro-2-nitrophenyl)acetate

생성물 1

HCID 37343717-Fluoro-2,3-dihydro-1h-indol-2-one수율 58%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
60 °C

실험 절차

To a 250 mL round bottom flask was added ethyl 2-(3-fluoro-2-nitrophenyl)acetate (3.1 g, 14 mmol), iron (3.8 g, 68 mmol), and 50 mL of AcOH. The reaction mixture was heated at 60° C. for 1 hour. The reaction mixture was concentrated and dissolved in 100 mL of EtOAc, filtered, and washed with 50 mL of a saturated NaHCO3 solution. The organic layer was concentrated and purified with silica gel column chromatography, eluting with 40% EtOAc/hexane to give 7-fluoroindolin-2-one (1.2 g, 58% yield) as a white solid. MS m/z: 152 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 3.58 (s, 2H), 6.94-7.04 (m, 3H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in 100 mL of EtOAc
  3. filtrationfiltered
  4. washwashed with 50 mL of a saturated NaHCO3 solution
  5. concentrationThe organic layer was concentrated
  6. custompurified with silica gel column chromatography
  7. washeluting with 40% EtOAc/hexane

출처 및 근거

ORD 기록
ord-008c352e667a4a35a82745b6f89e863d
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084479B2

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