Ammonium Hydroxide → 1-(4-Fluorophenyl)-4-oxo-7-(4-pyridyl)quinoline-3-carboxamide

HRID 1032717Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[CH:16]=3)[C:11](=[O:24])[C:10]([C:25](O)=[O:26])=[CH:9]2)=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:30]1C=CN=C1)=O.[OH-].[NH4+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[CH:16]=3)[C:11](=[O:24])[C:10]([C:25]([NH2:30])=[O:26])=[CH:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1.65 g 1-(4-fluorophenyl)-1,4-di-hydro4-oxo-7-(4-pyridinyl)-3-quinolinecarboxylic acid, 2.2 g of 1,1'-carbonyldiimidazole and 15 ml dimethylformamide (DMF) was heated at 150° C. for 1.5 hrs. The reaction mixture was poured into 50 ml concentrated ammonium hydroxide. The product was extracted with methylene dichloride and recovered therefrom to give 2.2 g 1-(4-fluorophenyl-1,4-dihydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxamide which was converted to its monomethanesulfonate salt hemihydrate, m.p. 301°-303° C. (decompn.). The free base, prepared from the salt with potassium carbonate solution, had m.p. 315°-317° C. when recrystallized from DMF.

Workup

extractionThe product was extracted with methylene dichloride
customrecovered

Sources & evidence

ORD record: ord-7afa9a36265f4142911d11889f04a977
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04959363

Reaction notes

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