Dimethylformamide → 1-[2-nitro-4-(trifluoromethyl)phenyl]pyrrolidine

HRID 2195634Notes

Reaction equation

HRID 2195634 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C=O.F[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23]>O>[N+:22]([C:13]1[CH:14]=[C:15]([C:18]([F:19])([F:20])[F:21])[CH:16]=[CH:17][C:12]=1[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 677784-Fluoro-3-nitrobenzotrifluoride

Product 1

HCID 27757531-[2-nitro-4-(trifluoromethyl)phenyl]pyrrolidineYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyrrolidine ((983 μl, 12.0 mmol, commercially available product) was added at 0° C. to a N,N-dimethylformamide (DMF; 4 ml) solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (1.02 g, 4.89 mmol, commercially available product). The resulting mixture was warmed to room temperature and stirred for 4.5 hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50 g, hexane/ethyl acetate=5/1). Thus, 1-[2-nitro-4-(trifluoromethyl)phenyl]pyrrolidine (1.26 g, 99.3%) was yielded as an orange-colored solid.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (50 g, hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-2676ccc82e3a40f4a18c286c97393475
Source dataset
uspto-grants-2012_12
Patent number
US08338362B2

Reaction notes

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