Diethyl (ethoxymethylene)malonate → HCID 178469532, compound

HRID 543695Notes

Reaction equation

HRID 543695 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].C([O:14][CH:15]=[C:16]([C:22](OCC)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>C(O)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:9]([C:15]([OH:14])=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:22]=[N:8]2)=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 793343-tert-Butylaniline

Product 1

HCID 178469532HCID 178469532, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-t-butylaniline (67.6 g.) and diethyl ethoxymethylenemalonate was heated on the steam bath for 3 hours, the ethanol formed being collected by distillation. The resulting yellow oil was dissolved in diphenyl ether (200 ml.) and added during 0.5 hour to stirred diphenyl ether (800 ml.) at 250°-260°, the ethanol formed being collected by distillation. The mixture was stirred at 250°-260° for 0.5 hour, then allowed to cool to room temperature and diluted with an equal volume of petroleum ether (b.p. 60°-80°). THe precipitate was collected by filtration to give the novel compound ethyl 7-t-butyl-4-hydroxyquinoline-3-carboxylate, m.p. 279°-281°.

Workup

  1. temperaturewas heated on the steam bath for 3 hours
  2. distillationbeing collected by distillation
  3. dissolutionThe resulting yellow oil was dissolved in diphenyl ether (200 ml.)
  4. additionadded during 0.5 hour
  5. customthe ethanol formed
  6. distillationbeing collected by distillation
  7. stirringThe mixture was stirred at 250°-260° for 0.5 hour
  8. additiondiluted with an equal volume of petroleum ether (b.p. 60°-80°)
  9. filtrationTHe precipitate was collected by filtration

Sources & evidence

ORD record
ord-fd817f20da124032b619978a4a75cf02
Source dataset
uspto-grants-1984_05
Patent number
US04447435

Reaction notes

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