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

HRID 77725Notes

Reaction equation

HRID 77725 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-e22b60ad790b457f9fb1c7c49e85232e
Source dataset
uspto-grants-2014_09
Patent number
US08841318B2

Reaction notes

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