Diethyl 2-[(4-fluoroanilino)methylene]malonate → Ethyl 6-fluoro-4-hydroxyquinoline-3-carboxylate

HRID 1944548Notes

Reaction equation

HRID 1944548 reaction equation
C(O[C:4](=[O:20])[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:20])[C:14]2[C:13](=[CH:18][CH:17]=[C:16]([F:19])[CH:15]=2)[NH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

3

Reactant 1

HCID 595792Diethyl 2-[(4-fluoroanilino)methylene]malonate

Product 1

HCID 710779Ethyl 6-fluoro-4-hydroxyquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

2-[(4-Fluoro-phenylamino)-methylene]-malonic acid diethyl ester (11.5 g, 40.9 mmol)) was added in portions to hot diphenylether (80 mL), while heating at reflux. The resultant mixture was heated an additional 2 hours, then allowed to cool to room temperature. A solid white precipitate developed. The mixture was diluted with heptanes, and the product was collected by filtration, washed with heptane, to give the product as a colorless crystalline solid, 3.0 g (31%). MS: m/z 235.9 (MH+).

Workup

  1. temperaturewhile heating
  2. temperatureat reflux
  3. filtrationthe product was collected by filtration
  4. washwashed with heptane

Sources & evidence

ORD record
ord-a42bf1859e64411c844e4090f7015842
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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