Ethanol → HCID 69270035, compound

HRID 77698Notes

Reaction equation

HRID 77698 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]([NH:17][C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)=[CH:4][CH:3]=1.C(O)C>[Fe].C(O)(=O)C>[NH2:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]([NH:17][C:18](=[O:29])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=3)[CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 69045292N-(6-Methyl-3'-nitrobiphenyl-3-yl)-3-(trifluoromethyl)benzamide

Product 1

HCID 69270035HCID 69270035, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To N-(6-methyl-3′-nitrobiphenyl-3-yl)-3-(trifluoromethyl)benzamide (1.00 g, 2.50 mmol) was added ethanol (18 mL) and acetic acid (1.7 mL) and iron (770 mg). The resulting mixture was heated to reflux until LCMS indicated complete reduction, typically 2-4 hours. The reaction was cooled to ambient temperature, and the unreacted iron was removed by filtration. The ethanolic filtrate was evaporated to dryness and EtOAc was added to the residue. The resulting rust-like particulates were removed by filtration through a small pad of diatomaceous earth, and the filtrate was evaporated to dryness to leave the crude aniline. The compound was recovered in quantitative yield and was used without further purification in the subsequent reaction. MS (EI) m/z=371 (M+H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux until LCMS
  3. customreduction, typically 2-4 hours
  4. customthe unreacted iron was removed by filtration
  5. customThe ethanolic filtrate was evaporated to dryness and EtOAc
  6. additionwas added to the residue
  7. customThe resulting rust-like particulates were removed by filtration through a small pad of diatomaceous earth
  8. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-711798a4e79a4f579b30fb6c9d5043ff
Source dataset
uspto-grants-2014_09
Patent number
US08841318B2

Reaction notes

Loading…