Acetic Acid → N-(3-(trifluoromethyl)benzyl)-2-(2-aminophenyl)isonicotinamide

HRID 625309Notes

Reaction equation

HRID 625309 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[CH2:6][NH:7][C:8](=[O:24])[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[CH:10]=1.C(O)(=O)C>C(O)C.O.[Fe]>[F:28][C:2]([F:1])([F:29])[C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[CH2:6][NH:7][C:8](=[O:24])[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH2:21])[CH:10]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66586876N-(3-(trifluoromethyl)benzyl)-2-(2-nitrophenyl)isonicotinamide

Product 1

HCID 66588070N-(3-(trifluoromethyl)benzyl)-2-(2-aminophenyl)isonicotinamideYield 80.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Into a 100-mL round bottom flask, was placed a solution of N-(3-(trifluoromethyl)benzyl)-2-(2-nitrophenyl)isonicotinamide (350 mg, 0.87 mmol, 1.00 equiv) in ethanol/H2O (1/1) (30 mL), iron (489 mg, 8.73 mmol, 10.00 equiv), and acetic acid (0.1 mL). The resulting solution was heated to reflux for 0.5 h. The solids were filtered out. The resulting solution was extracted with of ethyl acetate and the organic layers combined and dried over magnesium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The product was obtained as 260 mg (80%) of a yellow solid.

Workup

  1. customInto a 100-mL round bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 0.5 h
  4. filtrationThe solids were filtered out
  5. extractionThe resulting solution was extracted with of ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe solids were filtered out
  8. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-39dbcee27fd5437dbb950d0953898f43
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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