Dimethylformamide → HCID 53749379, compound

HRID 362597Notes

Reaction equation

[H-].[Na+].CN(C=O)C.[CH:8]1([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:24])=[C:18]([F:23])[C:19]=3[O:21][CH3:22])[C:14](=[O:25])[C:13]([C:26]([OH:28])=[O:27])=[CH:12]2)[CH2:10][CH2:9]1.[C:29]1([CH2:35]Cl)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.O>[CH2:35]([O:27][C:26]([C:13]1[C:14](=[O:25])[C:15]2[C:20](=[C:19]([O:21][CH3:22])[C:18]([F:23])=[C:17]([F:24])[CH:16]=2)[N:11]([CH:8]2[CH2:9][CH2:10]2)[CH:12]=1)=[O:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

NaH (2.6 g, 0.065 mol) was suspended and dissolved into DMF (dimethylformamide; 25 ml) and the reaction solution was stirred for about 10 minutes. A DMF solution (100 ml) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (I) (14 g, 0.047 mol) was slowly dropped therein. After the completion of adding, the reaction mixture was stirred at room temperature for about 10 minutes and further PhCH2Cl (benzylchloride; 6.0 ml, 0.052 mol) was dropped therein. The reaction mixture was heated on an oil bath at 100° C. for 6 hours. After the completion of heating, the reaction mixture was poured into water (500 ml) slowly to separate crystals. Separated crystals were washed with water three times and then with MeOH to obtain 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid benzyl ester (II) (13.6 g, yield: 74%).

Workup

additionAfter the completion of adding
stirringthe reaction mixture was stirred at room temperature for about 10 minutes
temperatureAfter the completion of heating
customto separate crystals
customSeparated crystals
washwere washed with water three times

Sources & evidence

ORD record: ord-618cd29bf4aa4a4c96936397d61ac31c
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869661

Reaction notes

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