Methyl 2-nitro-4-(trifluoromethyl)benzoate → Methyl 2-Amino-4-(trifluoromethyl)benzoate

HRID 507025Notes

Reaction equation

HRID 507025 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 11276727Methyl 2-nitro-4-(trifluoromethyl)benzoate

Product 1

HCID 12601886Methyl 2-Amino-4-(trifluoromethyl)benzoateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Add a solution of methyl 2-nitro-4-trifluoromethylbenzoate (106 g, 425 mmol) in ethyl acetate (2.2 L) to a slurry of 10% palladium on carbon (11.0 g) in ethyl acetate (200 mL) and stir the suspension at room temperature under an atmosphere of hydrogen at 60 psi for 3 h. Filter the suspension through a pad of Celite® and wash the pad with additional ethyl acetate. Remove the solvents under reduced pressure and purify the residue by column chromatography on silica gel, eluting with isohexane/ethyl acetate (9:1), to provide the title compound as a white crystalline solid (84 g, 95%). 1H NMR (300 MHz, CD3OD) δ 7.93 (d, J=8.48 Hz, 1H), 7.06 (s, 1H), 6.78 (s, 1H), 4.86 (s, 3H), 3.89 (s, 3H).

Workup

  1. filtrationFilter the suspension through a pad of Celite®
  2. washwash the pad with additional ethyl acetate
  3. customRemove the solvents under reduced pressure
  4. custompurify the residue by column chromatography on silica gel
  5. washeluting with isohexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-3367870ee0b84058a0acff8cc568d48f
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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