Ethanol → HCID 178469553, compound

HRID 2072391Notes

Reaction equation

HRID 2072391 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O:11][CH:12]=[C:13]([C:19](OCC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])C.C(O)C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[F:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][CH:3]=1)[N:6]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]2[OH:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 6871Diethyl (ethoxymethylene)malonateHCID 7583Diphenyl EtherHCID 97314-Fluoroaniline

Product 1

HCID 178469553HCID 178469553, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 66.6 g (0.6 mole) of 4-fluoroaniline and 129.79 g (0.6 mole) of diethyl ethoxymethylenemalonate was prepared under a nitrogen atmosphere and heated to 140° C. The ethanol generated was allowed to vaporize during a reaction time of about one hour. To the mixture was added 500 ml of diphenyl ether. The mixture was stirred and heated to its reflux temperature, and maintained at reflux for 15 minutes. The mixture was then cooled, and diethyl ether was added. The product was separated by filtration, washed with diethyl ether and air dried to provide 97.3 g (69% yield) of ethyl 6-fluoro-4-hydroxyquinoline-3-carboxylate.

Workup

  1. customwas prepared under a nitrogen atmosphere
  2. customto vaporize during a reaction time of about one hour
  3. temperatureheated to its
  4. temperaturereflux temperature
  5. temperaturemaintained
  6. temperatureat reflux for 15 minutes
  7. temperatureThe mixture was then cooled
  8. customThe product was separated by filtration
  9. washwashed with diethyl ether and air
  10. customdried

Sources & evidence

ORD record
ord-2b9c9de5ca924aa7b3eabf64720862cd
Source dataset
uspto-grants-1977_09
Patent number
US04051247

Reaction notes

Loading…