Diphenyl Ether → Ethyl 6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2227156Notes

Reaction equation

HRID 2227156 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]=[C:11]([C:17]([O:19]CC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[NH:9][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]2=[O:19]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 6189812-((4-Methoxy-phenylamino)-methylene)-malonic acid diethyl ester

Product 1

HCID 228284Ethyl 6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 44.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diethyl (4-methoxyphenylaminomethylene)malonate (5.18 g, 17.9 mmol) is added to phenyl ether (22 mL) preheated to 250° C. Heating is continued for 70 minutes. The reaction mixture is allowed to cool, diethyl ether is added, and the precipitate is collected, rinsed with diethyl ether and dried to afford 1.98 g of ethyl 6-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylate.

Workup

  1. custompreheated to 250° C
  2. temperatureHeating
  3. temperatureto cool
  4. customthe precipitate is collected
  5. washrinsed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-8da46fd8947643a2899290f8ec0d84cd
Source dataset
uspto-grants-2002_07
Patent number
US06413956B1

Reaction notes

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