Triethylamine → Ethyl 4-ethyl-7-fluoro-6-methoxy-2-oxo-1,2-dihydro-3-quinolinecarboxylate
Reaction equation
C([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])C.[NH2:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([O:18][CH3:19])=[CH:13][C:12]=1[C:20](=O)[CH2:21][CH3:22].C(N([CH2:29][CH3:30])CC)C.CC[O-:33].[Na+]>C(#N)C.O>[CH2:21]([C:20]1[C:12]2[C:11](=[CH:16][C:15]([F:17])=[C:14]([O:18][CH3:19])[CH:13]=2)[NH:10][C:7](=[O:8])[C:3]=1[C:4]([O:5][CH2:29][CH3:30])=[O:33])[CH3:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of ethylmalonyl chloride (12.9 ml, 100 mmol) in anhydrous acetonitrile (30 ml) is added dropwise, under argon and at 0° C. to a solution of 1-(2-amino-4-fluoro-5-methoxyphenyl)-1-propanone (15.3 g, 77.5 mmol) and triethylamine (13.9 ml, 100 mmol) in anhydrous acetonitrile (110 ml). The reaction medium is left to return to ambient temperature, a solution of sodium ethylate (obtained by 1.8 g, 78 mmol of sodium in 80 ml of ethanol) is cannulated dropwise and under argon, then the reaction medium is left under agitation for 12 hours at ambient temperature. The reaction mixture is poured into ice-cooled water (100 ml) and agitation is carried out for two hours, then the precipitate is filtered out and washed with water, with ethanol and with ether. 19.4 g of a white solid is obtained.
Workup
- waitThe reaction medium is left
- customto return to ambient temperature
- additionThe reaction mixture is poured into ice-
- waitis carried out for two hours
- filtrationthe precipitate is filtered out
- washwashed with water, with ethanol and with ether
Sources & evidence
- ORD record
- ord-62d32b041ea1483e999e6e9f76797894
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797715B1
Reaction notes
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