Diethyl (ethoxymethylene)malonate → HCID 14651160, compound

HRID 2396982Notes

Reaction equation

HRID 2396982 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([CH3:23])=[C:10]([C:15]([N+:20]([O-:22])=[O:21])=[C:16]([CH3:19])[C:17]=2[F:18])[NH:11][CH:12]2[CH2:14][CH2:13]2)[CH2:4][CH2:3]1.C(O[CH:27]=[C:28]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])C>>[CH2:32]([O:31][C:29](=[O:30])[C:28](=[CH:27][N:11]([CH:12]1[CH2:13][CH2:14]1)[C:10]1[C:15]([N+:20]([O-:22])=[O:21])=[C:16]([CH3:19])[C:17]([F:18])=[C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[C:9]=1[CH3:23])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH3:33]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 14651159HCID 14651159, compound

Product 1

HCID 14651160HCID 14651160, compound

Conditions

Temperature
150 °C

Procedure

To 3-(4-methyl-1-piperazinyl)-4-fluoro-2,5-dimethyl-6-nitro-N-cyclopropylaniline (1.65 g) is added diethyl ethoxymethylenemalonate (1.45 ml) and the mixture is heated at 150° C. for 25 hours. After cooling, the reaction product is purified by silica-gel column-chromatography (dichloromethane : methanol=100 : 1) to give diethyl[N-cyclopropyl-N-[3-(4-methyl-l-piperazinyl)-4 -fluoro-2,5-dimethyl-6-nitrophenyl]aminomethylene]malonate (1.58 g). The product is dissolved in acetic anhydride (7.9 ml) and thereto conc. sulfuric acid (3.16 ml) is added dropwise at 50°-60° C., followed by stirring for 30 minutes. The resultant mixture is poured into ice-water, neutralized, extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure. Purification by silica-gel column-chromatography (dichloromethane : methanol =10 : 1) and recrystallization from ethanol--diethyl ether to give ethyl 7-(4-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-5,8-dimethyl-1,4-dihydro-4 -oxoquinoline-3-carboxylate (28 mg), as yellow crystals, m.p. 146°-147° C.

Workup

  1. temperatureAfter cooling
  2. customthe reaction product is purified by silica-gel column-chromatography (dichloromethane : methanol=100 : 1)

Sources & evidence

ORD record
ord-361a8839f7a34801b738784fc544b09f
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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