Ethyl 2-(isonicotinoyl)-5-oxohexanoate → HCID 20295955, compound
Reaction equation
[O:1]=[C:2]([CH3:19])[CH2:3][CH2:4][CH:5]([C:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[O:12])C(OCC)=O.N1C=CC(C2CCCC(=O)C=2)=CC=1>>[N:16]1[CH:17]=[CH:18][C:13]([C:11](=[O:12])[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH3:19])=[CH:14][CH:15]=1Participants
Procedure
Gelotte et al. U.S. Pat. No. 4,111,946, issued Sept. 5, 1978, shows two sequences for converting ethyl 5-oxo-2-[(4-pyridinyl)carbonyl]hexanoate to 3-(4-pyridinyl)-2-cyclohexen-1-one: (1) heating ethyl 5-oxo-2-[(4-pyridinyl)-carbonyl]hexanoate under aqueous acidic conditions thereby hydrolyzing and decarboxylating it to produce 1-(4-pyridinyl)-hexan-1,5-dione and then reacting said hexan-1,5-dione with a basic condensing agent to produce 3-(4-pyridinyl)-2-cyclohexen-1-one; and, (2) reacting ethyl 5-oxo-2-[(4-pyridinyl)-carbonyl]hexanoate with a basic condensing agent to produce ethyl 3-(4-pyridinyl)-2-cyclohexen-1one-4-carboxylate and then heating said 4-carboxylate under aqueous acidic conditions to hydrolyze and decarboxylate it to produce 3-(4-pyridinyl)-2-cyclohexen-1-one. The 3-(4-pyridinyl)-2-cyclohexen-1one was then reacted with hydroxylamine to convert it into its oxime, an intermediate for preparing 3-(4-pyridinyl)aniline, in turn, an intermediate for preparing rosoxacin, an antibacterial agent, namely 1 -ethyl-1,4-dihydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxylic acid.
Sources & evidence
- ORD record
- ord-e4d1075b44674b24adb6bec58a8ebd8e
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04246420
Reaction notes
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