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

HRID 1805125Notes

Reaction equation

HRID 1805125 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-e2195e80c3e244439b58b9d9d1d97006
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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