Ethanol → HCID 178467010, compound

HRID 344891Notes

Reaction equation

HRID 344891 reaction equation
[F:1][C:2]1[C:18]([F:19])=[C:17]([F:20])[CH:16]=[CH:15][C:3]=1[N:4]=[C:5]([O:12][CH2:13][CH3:14])[CH2:6][C:7]([O:9]CC)=O.C(O)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:13]([O:12][C:5]1[CH:6]=[C:7]([OH:9])[C:15]2[C:3](=[C:2]([F:1])[C:18]([F:19])=[C:17]([F:20])[CH:16]=2)[N:4]=1)[CH3:14]

Participants

4

Reactant 2

HCID 702EthanolHCID 186419482,3,4-trifluoro-N-[1-ethoxy-2-(ethoxycarbonyl)ethylidene]aniline

Product 1

HCID 178467010HCID 178467010, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 2,3,4-trifluoro-N-[1-ethoxy-2-(ethoxycarbonyl)ethylidene]aniline (122 g) in phenyl ether (120 cc) is introduced dropwise in the course of 25 minutes and with stirring into phenyl ether (600 cc) at a temperature in the region of 250° C. while the ethanol formed is removed by distillation. After stirring for 15 minutes at the same temperature, the solution is cooled to approximately 20° C. and treated with n-hexane (750 cc). The precipitate formed is drained and washed with n-hexane (3×200 cc). 2-Ethoxy-6,7,8-trifluoro-4-hydroxyquinoline (69.5 g) is obtained in the form of a beige solid, m.p. 171° C., which is used without further purification for the subsequent steps.

Workup

  1. customformed
  2. customis removed by distillation
  3. additiontreated with n-hexane (750 cc)
  4. customThe precipitate formed
  5. washwashed with n-hexane (3×200 cc)

Sources & evidence

ORD record
ord-febe76dcc1d841188499f806e78c2608
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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