Diethyl (ethoxymethylene)malonate → HCID 178469532, compound

HRID 325647Notes

Reaction equation

HRID 325647 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-b402764ee18a4bac9e35e2861df7de72
Source dataset
uspto-grants-1984_04
Patent number
US04442109

Reaction notes

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