Pyrrolidine → 2-Nitro-5-methoxy-6-chloro-beta-pyrrolidinostyrene

HRID 1898992Notes

Reaction equation

HRID 1898992 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].N1CC[CH2:24][CH2:23]1>CN(C=O)C>[N+:9]([C:6]1[CH:5]=[CH:4][C:3]([O:12][CH3:13])=[C:2]([Cl:1])[C:7]=1[CH:8]=[CH:19][N:17]1[CH2:16][CH2:24][CH2:23][CH2:18]1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 137023832-Chloro-1-methoxy-3-methyl-4-nitrobenzene

Product 1

HCID 542523322-Nitro-5-methoxy-6-chloro-beta-pyrrolidinostyreneYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After reaction of 2-chloro-3-methyl-4-nitroanisole (32.1 g, 159 mmol) with dimethylformamide dimethylacetal (22.6 g, 190 mmol) and pyrrolidine (13.4 g, 188 mmol) in DMF (150 ml) at 120°-140° C. for 1 hour under a slow current of nitrogen, the volatile components were removed under vacuum. To the residue was added dichloromethane (90 ml) and methanol (360 ml) and the solution was evaporated to about half its original volume by heating on a steam bath. After cooling, the solution was left refrigerated overnight to yield 2-nitro-5-methoxy-6-chloro-β-pyrrolidinostyrene as red crystals (33.9 g) m.p. 89°-92° C.

Workup

  1. customthe volatile components were removed under vacuum
  2. additionTo the residue was added dichloromethane (90 ml) and methanol (360 ml)
  3. customthe solution was evaporated to about half its original volume
  4. temperatureby heating on a steam bath
  5. temperatureAfter cooling

Sources & evidence

ORD record
ord-da2f1591cdbd42f69a65626ca2f86002
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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