Pyrrolidine → HCID 59627932, compound

HRID 2421239Notes

Reaction equation

HRID 2421239 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17].N1CCCC1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1/[CH:12]=[CH:15]/[N:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 27733851-Bromo-5-fluoro-2-methyl-3-nitrobenzene

Product 1

HCID 59627932HCID 59627932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-bromo-5-fluoro-2-methyl-3-nitrobenzene (5.0 g, 21.37 mmol) in N,N-dimethylformamide (50 mL) was added N,N-dimethylformamide dimethyl acetal (8.58 mL, 64.1 mmol) and pyrrolidine(1.767 mL, 21.37 mmol). The reaction mixture was heated at 110° C. for 4 hours. After cooling to room temperature, the N,N-dimethylformamide was removed by evaporation. The residue was taken up in diethyl ether and water. After separation of the organic layer, the aqueous layer was re-extracted with diethyl ether. The combined organic layers were dried over magnesium sulphate, filtered and concentrated to give a red/brown oil which was used directly in the following reaction without purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe N,N-dimethylformamide was removed by evaporation
  3. customAfter separation of the organic layer
  4. extractionthe aqueous layer was re-extracted with diethyl ether
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a red/brown oil which
  9. customwas used directly in the following reaction without purification

Sources & evidence

ORD record
ord-ba1d3cf91f75493fb2e02562d22772cc
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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