tert-Butanol → 6,8-Difluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

HRID 1085783Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:18])[C:11]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[N:8]1[CH:19]([CH3:21])[S:20][C:7]1=[C:6]([C:22]([O:24]CC)=[O:23])[C:5]2=[O:27].[OH-].[K+].C(O)(C)(C)C>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:18])[C:11]=1[N:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)[N:8]1[CH:19]([CH3:21])[S:20][C:7]1=[C:6]([C:22]([OH:24])=[O:23])[C:5]2=[O:27]

Participants

Conditions

Temperature: 60 °C

Procedure

To 0.5 g of ethyl 6,8-difluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate was added 10 ml of 5% solution of potassium hydroxide in a 3:1 mixture of tert-butanol and water and the mixture was stirred at 60° C. for 30 minutes. tert-Butanol was evaporated therefrom in vacuo and the residue was neutralized with acetic acid. After cooling, the crystals separated out therefrom were collected by filtration, washed with water and then washed with acetone and ether to give 0.43 g of the title product, m.p. 260° C. (decompn.).

Workup

customtert-Butanol was evaporated
temperatureAfter cooling
customthe crystals separated out
filtrationtherefrom were collected by filtration
washwashed with water
washwashed with acetone and ether

Sources & evidence

ORD record: ord-3f8bc9ea90af4344b2e23845e1db3f16
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05011831

Reaction notes

Loading…