N-methyl-2-pyrrolidone → HCID 9865818, compound

HRID 2084986Notes

Reaction equation

HRID 2084986 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].Cl[C:11]1[C:12](=[O:26])[NH:13][C:14](=[O:25])[C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1.CN1CCCC1=O>Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:11]2[C:12](=[O:26])[NH:13][C:14](=[O:25])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 82187Benzenamine, 3-bromo-4-methyl-HCID 22728657HCID 22728657, compound

Product 1

HCID 9865818HCID 9865818, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 3-bromo-4-methylaniline (0.220 g, 1.18 mmol), 3-chloro-4-(3-nitrophenyl)-1H-pyrrole-2,5-dione (0.100 g, 0.40 mmol) and 1-methyl-2-pyrrolidinone (1.0 mL) was heated in an oil bath at 200° C., for 51 minutes. The mixture was diluted with aqueous hydrochloric acid (5 mL) and extracted with ethyl acetate (5 mL). The combined organic solutions were evaporated and the residue chromatographed on silica gel using dichloromethane as eluent to afford the title compound, a solid, following trituration with dichloromethane-hexane (90:10 v/v).

Workup

  1. extractionextracted with ethyl acetate (5 mL)
  2. customThe combined organic solutions were evaporated
  3. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-338ce92cfa2f4c718392be35db33585b
Source dataset
uspto-grants-2004_04
Patent number
US06719520B2

Reaction notes

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