Methanol → HCID 150640, compound

HRID 904664Notes

Reaction equation

HRID 904664 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]3[O:15][C:14]([C:16]([O:18]CC)=[O:17])=[CH:13][C:12](=[O:21])[C:9]=3[CH:10]=2)[N:5]=[C:4]([C:25]([O:27]C)=[O:26])[CH:3]=1.CO.[OH-].[Na+].O>C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]3[O:15][C:14]([C:16]([OH:18])=[O:17])=[CH:13][C:12](=[O:21])[C:9]=3[CH:10]=2)[N:5]=[C:4]([C:25]([OH:27])=[O:26])[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 13543928HCID 13543928, compound

Product 1

HCID 150640HCID 150640, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 6-chloro-8-methoxycarbonyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate (1.313 g) was suspended in refluxing methanol (300 mls) and 0.1 M sodium hydroxide solution (65 mls) was added dropwise, with stirring. The whole was then refluxed for ten minutes, cooled, poured into water and acidified. The precipitated product was extracted into ethyl acetate, washed with water, dried with magnesium sulphate, filtered and volatiles removed in vacuo, affording 1.05 g of the crude sub-title compound as a yellow solid. This yellow solid was dissolved in sodium bicarbonate solution, filtered and the filtrate acidified. The precipitated product was collected by filtration, washed with water and dried to give 0.77 g of the sub-title compound. MP 340° C.

Workup

  1. additionwas added dropwise
  2. temperatureThe whole was then refluxed for ten minutes
  3. temperaturecooled
  4. extractionThe precipitated product was extracted into ethyl acetate
  5. washwashed with water
  6. dry with materialdried with magnesium sulphate
  7. filtrationfiltered
  8. customvolatiles removed in vacuo
  9. customaffording 1.05 g of the crude sub-title compound as a yellow solid
  10. filtrationfiltered
  11. filtrationThe precipitated product was collected by filtration
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-4161e12a5d3144099bffa40097b9b8db
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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