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

HRID 58199

反応式

HRID 58199 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
200 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-fdc4f6b5c93549c096c14e068b7f3621
出典データセット
uspto-grants-2016_09
特許番号
US09434697B2

関連ノート

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