Pyrrolidine → HCID 5908071, compound

HRID 656060Notes

Reaction equation

HRID 656060 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][N:13]([CH:15](OC)OC)[CH3:14].N1CC[CH2:22][CH2:21]1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:12]/[N:13]2[CH2:15][CH2:22][CH2:21][CH2:14]2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 679654-Fluoro-2-nitrotolueneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5908071HCID 5908071, compoundYield 108.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 4-fluoro-2-nitrotoluene (50.0 g, 0.327 mol) in DMF (100 mL) was added DMF-DMA (52 mL, 0.392 mol) and pyrrolidine (33 ml, 0.392 mol) in DMF (100 mL). The reaction mixture was stirred at reflux overnight and then concentrated under reduced pressure, giving 84 g of the title compound.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5cab36b2d4542a5b70b48a2f53aa5e9
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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