Acetic Acid → 3'-Amino-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

HRID 1894897Notes

Reaction equation

HRID 1894897 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)=[CH:6][C:5]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[O:18])=[CH:4][CH:3]=1.C(O)(=O)C>C(O)C.[Fe]>[NH2:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)=[O:18])[CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 692737816-methyl-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

Product 1

HCID 690436683'-Amino-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To 6-methyl-3′-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide (0.90 g, 2.2 mmol) in ethanol (22 mL) was added acetic acid (2 mL) and iron (0.90 g, 16 mmol) and the resulting mixture was heated to reflux for 1 hour. Solvent was removed in vacuo. Ethyl acetate was added and solids were removed by filtration. The filtrate was washed sequentially with saturated sodium bicarbonate and brine, dried (Na2SO4) and then concentrated. The product was used without further purification (850 mg, 95%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 1 hour
  3. customSolvent was removed in vacuo
  4. additionEthyl acetate was added
  5. customsolids were removed by filtration
  6. washThe filtrate was washed sequentially with saturated sodium bicarbonate and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe product was used without further purification (850 mg, 95%)

Sources & evidence

ORD record
ord-35352d55140142bdbc4c6a05cc0a6d38
Source dataset
uspto-grants-2013_08
Patent number
US08513270B2

Reaction notes

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