Water → 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-Carboxylic Acid

HRID 600871Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:18]([O:20]CC)=[O:19])=[CH:6][N:7]2[C@@H:14]1[CH2:16][C@@H:15]1[F:17].O.S(=O)(=O)(O)O>C(O)(=O)C>[NH2:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[C@@H:14]1[CH2:16][C@@H:15]1[F:17]

Participants

Conditions

Temperature: 120 °C

Procedure

Ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate (735 mg, 2.28 mmol) was dissolved in a 1:1 mixed solution (8 ml) of acetic acid:water, and after adding concentrated sulfuric acid (90 μl) thereto, it was stirred for 4 hours in an oil bath of 120° C. After cooling the reaction solution with ice, water (20 ml) was poured therein, and the mixed reaction solution was stirred at room temperature for 2 hours. The precipitated crystals were filtered out, washed with excess water, a small amount of cold ethanol and excess diethyl ether in that order, and then dried under a reduced pressure at 80° C. for 17 hours. 552 mg (82%) of the title compound was thereby obtained in the form of yellow crystals.

Workup

additionwas poured
customthe mixed reaction solution
stirringwas stirred at room temperature for 2 hours
filtrationThe precipitated crystals were filtered out
washwashed with excess water
dry with materiala small amount of cold ethanol and excess diethyl ether in that order, and then dried under a reduced pressure at 80° C. for 17 hours

Sources & evidence

ORD record: ord-b8556ed33a384ad7bfad3ff57897d494
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902226B2

Reaction notes

Loading…