Sodium Bicarbonate → 3-Nitro-4-(trifluoromethyl)aniline

HRID 2404864Notes

Reaction equation

HRID 2404864 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[C:8]([N+:16]([O-:18])=[O:17])[CH:7]=1)=O.C([O-])(O)=O.[Na+]>Cl>[N+:16]([C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[C:12]([F:13])([F:14])[F:15])[NH2:5])([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67246719HCID 67246719, compound

Product 1

HCID 164327543-Nitro-4-(trifluoromethyl)anilineYield 97%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2,2-dimethyl-N-[3-nitro-4-(trifluoromethyl)phenyl]propanamide (45.0 g, 155.0 mmol) in 6N HCl (200 mL) was stirred at 100° C. overnight. The reaction mixture was cooled to room temperature and was carefully neutralized with solid NaHCO3 to pH=9. The reaction mixture was extracted with CH2Cl2 and dried over Na2SO4. The solvent was evaporated in vacuo to obtain the crude product 3-nitro-4-(trifluoromethyl)aniline (31.0 g, 97%), which was used directly for the next step.

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-462aee9231394ec793e446ddb4d085e3
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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