4-Fluoro-3-nitrobenzoic acid → 4-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrobenzoic acid

HRID 1950813Notes

Reaction equation

HRID 1950813 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][CH:15]1[CH2:19][CH2:18][CH:17]([CH3:20])[NH:16]1>>[CH3:14][CH:15]1[CH2:19][CH2:18][CH:17]([CH3:20])[N:16]1[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 679874-Fluoro-3-nitrobenzoic acidHCID 960342,5-Dimethylpyrrolidine

Product 1

HCID 596065544-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrobenzoic acidYield 84.1%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoro-3-nitrobenzoic acid (300 mg; 1.62 mmol; 1 eq.) and 2,5-dimethylpyrrolidine (Maybridge AC11676DA; 0.70 mL; 5.72 mmol; 3.53 eq.) was stirred at 100° C. for 5 minutes in the MW. The solution was concentrated in vacuo and the residue taken up in water (100 mL). The aqueous phase was washed with diethyl ether (2×20 mL) then acidified to pH 5 with acetic acid. Extraction with diethyl ether (150 mL), drying over magnesium sulfate and concentration in vacuo afforded the title compound (360 mg, 84%) as an orange solid.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washThe aqueous phase was washed with diethyl ether (2×20 mL)
  3. extractionExtraction with diethyl ether (150 mL)
  4. dry with materialdrying over magnesium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-26b9fe06815d4617ae4ecd42d329ecb9
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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