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

HRID 58199

Reaction equation

HRID 58199 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-fdc4f6b5c93549c096c14e068b7f3621
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

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