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Diethyl Ether → Diethyl 6-ethylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate

HRID 904694
Notes
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Reaction equation

HRID 904694 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:8]=[C:7]2[NH:23][CH2:24][CH3:25])(=[O:3])[CH3:2].[C:26](OCC)(=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28].CCOCC.[H-].[Na+]>CN(C)C=O.Cl.O>[CH2:24]([NH:23][C:7]1[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]3[O:14][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:2][C:1](=[O:3])[C:4]=3[CH:5]=2)[N:10]=[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:8]=1)[CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 135773208HCID 135773208, compound

Product 1

HCID 20478396Diethyl 6-ethylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylateYield 55%

Reagents, catalysts & solvents 3

HCID 313
Hydrochloric Acid
Solvent
2×
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of step (b) (2.2 g; 6.3953 mmoles) and diethyl oxalate (8.5 g; 58.2191 mole) in dry dimethylformamide (50 ml) was added slowly to a stirred suspension of ether washed sodium hydride (0.38 g, 15.83 mmole) under nitrogen. After the addition, the mixture was allowed to stir under nitrogen for 72 hours. The mixture was poured onto ice, followed by acidification with dilute hydrochloric acid. The pH of the mixture was adjusted to about 7 before extraction into ethyl acetate. The extract was washed with water, dried and evaporated to give a light yellow solid. The solid was dissolved in ethanolic hydrochloric acid and heated to reflux on a steambath for 3 hours. The mixture was cooled, and treated with water. This was then concentrated and the pH of the mixture was adjusted to about 7, followed by extraction with ethyl acetate. The extract was washed, dried and evaporated to give a brown solid (2 g; 74%). The solid was recrystallised from ethanol to give a light brown solid (1.5 g).

Workup

  1. additionAfter the addition
  2. additionThe mixture was poured onto ice
  3. extractionThe pH of the mixture was adjusted to about 7 before extraction into ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated
  7. customto give a light yellow solid
  8. temperatureheated
  9. temperatureto reflux on a steambath for 3 hours
  10. temperatureThe mixture was cooled
  11. concentrationThis was then concentrated
  12. extractionfollowed by extraction with ethyl acetate
  13. washThe extract was washed
  14. customdried
  15. customevaporated
  16. customto give a brown solid (2 g; 74%)
  17. customThe solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-afbf9499379c4d0085faf9ffc157ad04
Source dataset
uspto-grants-1983_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04419352

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes