Isonicotinic Acid → N-[2-(4-Methoxyphenyl)-2-oxoethyl]-4-pyridinecarboxamide

HRID 1728998Notes

Reaction equation

HRID 1728998 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Cl-].[CH3:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17](=[O:20])[CH2:18][NH3+:19])=[CH:15][CH:14]=1>S(Cl)(Cl)=O>[C:1]([NH:19][CH2:18][C:17]([C:16]1[CH:21]=[CH:22][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1)=[O:20])(=[O:9])[C:2]1[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5922Isonicotinic AcidHCID 167405372-(4-Methoxyphenyl)-2-oxoethanaminium chloride

Product 1

HCID 9993270N-[2-(4-Methoxyphenyl)-2-oxoethyl]-4-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Isonicotinic acid (24.93 g., 0.0938 mole) and thionyl chloride (50 ml) is refluxed for 1 hour. The crude acid chloride which remains after removal of excess thionyl chloride at diminished pressure is dissolved in dry pyridine (200 ml) and p-methoxy phenacylammonium chloride (19.00 g, 0.938 mole) is added portion wise to the stirred solution. The addition is exothermic.. After the addition is completed, the reaction mixture is heated and stirred on a boiling water bath for 2 hours and then poured into ice-water to precipitate the product. The solid is collected and dried under reduced pressure to give α-isonicotinamido-p-methoxyacetophenone m.p. 227°-230° C. (with decomposition). α-isonicotinamido-p-methoxyacetophenone (11.5 g., 0.043 mole) is added portion-wise to a stirred solution of 200 ml of acetic anhydride and 15 ml of 90% phosphoric acid; the addition is exothermic. After the addition is complete the reaction mixture is stirred and refluxed for 2 hours. After cooling, the supernatant liquid is decanted from the viscous precipitate, which is crystallized by titration with 350 ml of 1% aqueous sodium hydroxide. The yellow solid is filtered, washed with distilled water (200 ml), and dried in vacuo yielding 2-(4-pyridyl)-5-p-methoxyphenyloxazole, m.p. 105°-107° C.

Workup

  1. customafter removal of excess thionyl chloride at diminished pressure
  2. dissolutionis dissolved in dry pyridine (200 ml)
  3. additionThe addition
  4. additionAfter the addition
  5. temperaturethe reaction mixture is heated
  6. customto precipitate the product
  7. customThe solid is collected
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-7bdd271cb0124e30a2e7554028e4c1f8
Source dataset
uspto-grants-1994_07
Patent number
US05329540

Reaction notes

Loading…