Trifluoroacetic acid → 4-(2-Nitrophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid

HRID 454750Notes

Reaction equation

HRID 454750 reaction equation
FC(F)(F)C(O)=O.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23]C(C)(C)C)=[O:22])=[C:19]([NH:30][C:31]([C:33]2[CH:34]=[N:35][CH:36]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:38]=2)=[O:32])[CH:18]=1)([O-:10])=[O:9]>>[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:29]=[CH:28][C:20]([C:21]([OH:23])=[O:22])=[C:19]([NH:30][C:31]([C:33]2[CH:34]=[N:35][CH:36]=[C:37]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:38]=2)=[O:32])[CH:18]=1)([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508723Tert-butyl 4-(2-nitrophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate

Product 1

HCID 585087724-(2-Nitrophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acidYield 77.9%

Procedure

Trifluoroacetic acid (3.0 mL) was added to tert-butyl 4-(2-nitrophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate (68 mg), followed by stirring at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration, and dioxane (3.0 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.053 mL) were sequentially added to the obtained solid substance, followed by stirring at room temperature for 1 hour and 50 minutes. Water was added to the reaction mixture. After adjusting the pH to 6.3 with 1 mol/L hydrochloric acid, the solid substance was collected by filtration to obtain 47 mg of 4-(2-nitrophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  2. additionwas added to the obtained residue
  3. filtrationThe solid substance was collected by filtration, and dioxane (3.0 mL)
  4. additiona 2 mol/L aqueous solution of sodium hydroxide (0.053 mL) were sequentially added to the obtained solid substance
  5. stirringby stirring at room temperature for 1 hour and 50 minutes
  6. additionWater was added to the reaction mixture
  7. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-f24aa22dd3404fc2a19ae402359ed5e5
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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