N-methyl-2-pyrrolidone → 2-(4-Bromo-2-nitrophenyl)isoindoline-1,3-dione

HRID 58199

반응식

HRID 58199 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N-:14]1.[K+].CN1C(=O)CCC1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:14]2[C:15](=[O:22])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]2=[O:12])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

참가 물질

5

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 3356745Potassium phthalimide

생성물 1

HCID 1180254582-(4-Bromo-2-nitrophenyl)isoindoline-1,3-dione수율 92%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
200 °C

실험 절차

4-bromo-1-fluoro-2-nitrobenzene (2.0 g, 9.1 mmol) and potassium 1,3-dioxoisoindolin-2-ide (2.0 g, 10.9 mmol) were placed in microwave vial (0.5-2 ml) and NMP (12.0 ml) was added. The reaction mixture was heated at 200° C. using microwave (Biotage, Initiator) for 1 min. After cooling to rt, the reaction mixture was added dropwise to stirring water which resulted in formation of precipitate. The solid was collected, washed with water and dried under stream of nitrogen to afford the title compound (2.89 g, yield: 92%). 1H-NMR (400 MHz, CDCl3) δ 7.26 (s, 2H) 7.43 (d, 2H) 7.81-7.87 (m, 3H) 7.91 (dd, 2H) 7.95-8.05 (m, 3H) 8.33 (d, 1H)

후처리

  1. additionwas added
  2. customfor 1 min
  3. temperatureAfter cooling to rt
  4. additionthe reaction mixture was added dropwise
  5. customresulted in formation of precipitate
  6. customThe solid was collected
  7. washwashed with water
  8. customdried under stream of nitrogen

출처 및 근거

ORD 기록
ord-fdc4f6b5c93549c096c14e068b7f3621
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434697B2

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