Hydrochloric Acid → 4-[3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoic acid

HRID 874770Notes

Reaction equation

HRID 874770 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:27]([F:30])([F:29])[F:28])[CH2:13][CH2:12][N:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[C:16]([N+:24]([O-:26])=[O:25])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].Cl>O1CCOCC1>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:27]([F:29])([F:30])[F:28])[CH2:13][CH2:12][N:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[C:16]([N+:24]([O-:26])=[O:25])[CH:15]=3)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58218897Methyl 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoate

Product 1

HCID 582188794-[3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoic acidYield 70.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To the solution of methyl 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoate (1.24 g) in 1,4-dioxane was added 2N aqueous sodium hydroxide (5.4 mL), and the mixture was heated with stirring at 80° C. The mixture was cooled to room temperature and then acidified with 2N hydrochloric acid before the mixture was extracted twice with ethyl acetate. The organic layer was combined, which was then washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure to yield 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoic acid (0.85 g). 1H-NMR (DMSO-d6) δ: 2.58-2.72 (1H, m), 2.91-3.04 (1H, m), 3.47-3.57 (2H, m), 3.87 (1H, d), 4.32 (1H, d), 6.86 (1H, dd), 7.04 (1H, d), 7.65 (2H, d), 7.71 (1H, t), 7.78 (1H, d)

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. extractionwas extracted twice with ethyl acetate
  4. washwhich was then washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. distillationthe solvent was distilled away under the reduced pressure

Sources & evidence

ORD record
ord-b9c7b2a217eb4a439b3f0a9d0c2c9c62
Source dataset
uspto-grants-2015_03
Patent number
US08980937B2

Reaction notes

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