Diethyl (ethoxymethylene)malonate → HCID 178469649, compound

HRID 2290040Notes

Reaction equation

HRID 2290040 reaction equation
[CH2:1]([S:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([F:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C.CCCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:1]([S:8][C:9]1[CH:15]=[C:14]2[C:12](=[C:11]([F:16])[CH:10]=1)[N:13]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]2[OH:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 8900HeptaneHCID 18698512HCID 18698512, compound

Product 1

HCID 178469649HCID 178469649, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
135 °C

Procedure

A neat mixture of 3.58 g of compound of 4-(benzylsulfanyl)-2-fluoroaniline and 3.48 g of diethyl ethoxymethylenemalonate is heated at 135° C. under a slow argon sweep for 1 h, then diluted with 25 mL of diphenyl ether and heated to 260° C., with maintenance of the argon sweep, and kept at that temperature for 90 min. The mixture is then cooled to ca 100° C. and added to 300 mL of stirred heptane. The precipitate is filtered, washed with heptane, and dried in vacuo to provide 4.01 g of ethyl 6-(benzylsulfanyl)-8-fluoro-4-hydroxy-3-quinolinecarboxylate as a yellow solid.

Workup

  1. temperatureheated to 260° C., with maintenance of the argon sweep
  2. temperatureThe mixture is then cooled to ca 100° C.
  3. filtrationThe precipitate is filtered
  4. washwashed with heptane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-df8c20ff9d1b4227b7379333bc141605
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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