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

HRID 1915467Notes

Reaction equation

HRID 1915467 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-300779adb89142f482a0695894268610
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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