Triethylamine → 7-Fluoro-1-methyl-4-oxo-1,4-dihydro-quinol-3-yl ethanesulphonate
Reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[F:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:20])[C:13]([OH:19])=[CH:14][N:15]2[CH3:18])=[CH:10][CH:9]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([S:3]([O:19][C:13]1[C:12](=[O:20])[C:11]2[C:16](=[CH:17][C:8]([F:7])=[CH:9][CH:10]=2)[N:15]([CH3:18])[CH:14]=1)(=[O:5])=[O:4])[CH3:2]Participants
Procedure
Ethanesulphonyl chloride (1.5 ml) was added to a stirred mixture of 7-fluoro-3-hydroxy-1-methyl-4quinolone (3.0 g), obtained as described in Example 3a-f, triethylamine (4.35 ml) and dry dichloromethane (100 ml) at ambient temperature and the resultant solution stirred for 5 minutes then kept at ambient temperature overnight. Further ethanesulphonyl chloride (0.2 ml) was added and the solution stirred at ambient temperature for 4 hours and then kept at this temperature for 3 days. The mixture was filtered and the filtrate was washed with water (2×150 ml). The dichloromethane solution was dried over magnesium sulphate and the solvent evaporated to give a residue which was crystallised from industrial methylated spirit (100 ml). The solid was triturated with diethyl ether (100 ml) and then water (500 ml) to give the novel compound 7-fluoro-1-methyl-4-oxo-1,4-dihydro-quinol-3-yl ethanesulphonate, m.p. 154°-156.5°.
Workup
- customobtained
- waitkept at this temperature for 3 days
- filtrationThe mixture was filtered
- washthe filtrate was washed with water (2×150 ml)
- dry with materialThe dichloromethane solution was dried over magnesium sulphate
- customthe solvent evaporated
- customto give a residue which
- customwas crystallised from industrial methylated spirit (100 ml)
- customThe solid was triturated with diethyl ether (100 ml)
Sources & evidence
- ORD record
- ord-12525b913ada47238664b5f691b20e09
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04997840
Reaction notes
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