Diethyl (ethoxymethylene)malonate → HCID 13491701, compound
Reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH3:11])[CH3:2].C([O:14][CH:15]=[C:16]([C:22](OCC)=O)[C:17]([O:19]CC)=[O:18])C>O>[CH2:1]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([F:10])[C:5]=2[CH3:11])[C:15](=[O:14])[C:16]([C:17]([OH:19])=[O:18])=[CH:22]1)[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
Nine grams of N-ethyl-2-methyl-3-fluoroaniline is allowed to react with 15 g of diethyl ethoxymethylenemalonate under heating at 110° C. for 30 minutes. Then, polyphosphoric acid (obtained from 50 g each of phosphoric acid and phosphorus pentaoxide) is added to be subjected to the reaction at 140° C. for 40 minutes. After the reaction is completed, the mixture is poured into 600 g of water and ice to obtain crystals. The crystals are recovered by filtration, and a 10% sodium hydroxide solution is added to the filtrate and the mixture is refluxed for 1 hour. After refluxing, the reaction mixture is treated with activated carbon and adjusted to pH 2 with concentrated hydrochloric acid, whereby there separate out light yellow crystals. Recrystallization from dimethylformamide yields 10 g of 1-ethyl-7-fluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid as the white, needle-like crystals. mp. 245°-246° C.
Workup
- customto be subjected to the reaction at 140° C. for 40 minutes
- customto obtain crystals
- filtrationThe crystals are recovered by filtration
- additiona 10% sodium hydroxide solution is added to the filtrate
- temperaturethe mixture is refluxed for 1 hour
- temperatureAfter refluxing
- additionthe reaction mixture is treated with activated carbon
- customseparate out light yellow crystals
- customRecrystallization from dimethylformamide
Sources & evidence
- ORD record
- ord-ce77a204b2404c6c9356ea90130a00f3
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04544747
Reaction notes
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