2-Methylpyridine → Ethyl 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2418469Notes

Reaction equation

HRID 2418469 reaction equation
N1C=CC=CC=1C.[CH3:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH2:15]([O:17][C:18]([C:20]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][C:25](Cl)=[C:26]([F:31])[CH:27]=2)[N:22]([CH2:33][CH3:34])[CH:21]=1)=[O:19])[CH3:16]>>[CH2:15]([O:17][C:18]([C:20]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][C:25]([N:12]3[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]3)=[C:26]([F:31])[CH:27]=2)[N:22]([CH2:33][CH3:34])[CH:21]=1)=[O:19])[CH3:16]

Participants

4

Reactant 3

HCID 79752-MethylpyridineHCID 531671-MethylpiperazineHCID 12733855Ethyl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Product 1

HCID 1068705Ethyl 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 64.8%

Procedure

A mixture of 8 ml of α-picoline, 4.8 g of 1-methylpiperazine, and 3.6 g of 1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester was refluxed for 5 hrs. The reaction mixture was treated by operating as in Example 6 to give 2.8 g (64.8% yield) of 1-ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester. mp: 176°-177° C. The above ethyl ester was hydrolyzed by the same way in Example 1 to obtain the corresponding acid.

Workup

  1. temperaturewas refluxed for 5 hrs
  2. additionThe reaction mixture was treated

Sources & evidence

ORD record
ord-602cb7fe211e43d0a01ca4a801f47d88
Source dataset
uspto-grants-1984_09
Patent number
US04472579

Reaction notes

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