Ethanol → HCID 178469553, compound

HRID 1283803Notes

Reaction equation

HRID 1283803 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-d4c5b164ee69422c8232fcd48501a2f1
Source dataset
uspto-grants-1976_08
Patent number
US03976651

Reaction notes

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