Diethyl Malonate → Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 1947108Notes

Reaction equation

HRID 1947108 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:12](OCC)(=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[O-]CC.[Na+]>C(O)C>[OH:10][C:1]1[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:4][C:12](=[O:19])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8635Methyl AnthranilateHCID 2723922Sodium ethoxide

Product 1

HCID 54684458Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylateYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of methyl anthranilate (121 g, 0.8 mol) and diethyl malonate (128 g, 0.8 mol) in ethanol (900 mL) was added a 20% solution (274 g) of sodium ethoxide in ethanol, and the mixture was stirred at room temperature for 30 min. Ethanol was evaporated, and the mixture was stirred at 140° C. for 12 hr. After cooling, the obtained solid was washed with diethyl ether, and dissolved in water. Insoluble materials were filtered off, the filtrate was acidified with 5N hydrochloric acid, and the precipitated solid was collected by filtration. The obtained solid was washed with water, and dried under reduced pressure to give the title compound (161 g, 86%) as a pale-yellow powder.

Workup

  1. customEthanol was evaporated
  2. stirringthe mixture was stirred at 140° C. for 12 hr
  3. temperatureAfter cooling
  4. washthe obtained solid was washed with diethyl ether
  5. dissolutiondissolved in water
  6. filtrationInsoluble materials were filtered off
  7. filtrationthe precipitated solid was collected by filtration
  8. washThe obtained solid was washed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-b5faaf1b461046bb986a9d911bd85954
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

Loading…