Diethyl (ethoxymethylene)malonate → HCID 178469641, compound

HRID 2290049Notes

Reaction equation

HRID 2290049 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].C([O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[OH:12][C:13]1[C:7]2[C:5](=[CH:4][C:3]([S:2][CH3:1])=[CH:9][CH:8]=2)[N:6]=[CH:20][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 15693Benzenamine, 3-(methylthio)-

Product 1

HCID 178469641HCID 178469641, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
135 °C

Procedure

A neat mixture of 2.8 g of compound of 3-methylthioaniline and 4.0 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 1:1 ether-hexane. The precipitate is filtered, washed with hexane, and dried in vacuo to provide 1.35 g of crude material as a tan solid, which is recrystallized from acetic acid-water to afford 1.06 g of ethyl 4-hydroxy-7-(methylsulfanyl)-3-quinolinecarboxylate.

Workup

  1. temperatureheated to 260° C., with maintenance of the argon sweep
  2. temperatureThe mixture is then cooled to ca 100° C.
  3. additionadded to 300 mL
  4. filtrationThe precipitate is filtered
  5. washwashed with hexane
  6. customdried in vacuo
  7. customto provide 1.35 g of crude material as a tan solid, which
  8. customis recrystallized from acetic acid-water

Sources & evidence

ORD record
ord-0aa257aed59c43adbdc1a37ba9a507b9
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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