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

HRID 2164692Notes

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

Conditions

Temperature: 40 °C

Procedure

Isonicotinic acid (24.93 g., 0.0938 mole) and thionyl chloride (50 ml) was refluxed for 1 hour. The crude acid chloride which remained after removal of excess thionyl chloride at diminished pressure was dissolved in dry pyridine (200 ml) and p-methoxy phenacylammonium chloride (19.00 g, 0.938 mole) was added portion wise to the stirred solution. During the addition, an exotherm occurred which raised the temperature of the stirred mixture to 40° C. After the addition was completed, the reaction mixture was heated and stirred on a boiling water bath for 2 hours and then poured into ice-water to precipitate the product. The solid was collected and dried under reduced pressure to give 12.07 g. (yield 48%) of α-isonicotinamido-p-methoxyacetophenone m.p. 227°-230° C. (with decomposition).

Workup

customafter removal of excess thionyl chloride at diminished pressure
dissolutionwas dissolved in dry pyridine (200 ml)
additionDuring the addition
additionAfter the addition
temperaturethe reaction mixture was heated
customto precipitate the product
customThe solid was collected
customdried under reduced pressure
customto give 12.07 g

Sources & evidence

ORD record: ord-0096db1fe90e46dc905d63c9b66b3741
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04506368

Reaction notes

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