Hydrochloric Acid → HCID 12802705, compound

HRID 1448818Notes

Reaction equation

HRID 1448818 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[CH:9][C:8]2=[O:18])=[CH:4][CH:3]=1.[H-].[Na+].CO.Cl.[C:26](=O)([O:30]CC)[O:27]CC>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][C:26]([OH:30])=[O:27])=[CH:9][C:8]2=[O:18])=[CH:19][CH:20]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 12114996N-350S

Product 1

HCID 12802705HCID 12802705, compoundYield 15%

Procedure

A solution of 1-(4-chlorobenzyl)-1,2-dihydro-4-methyl-2-oxoquinoline (18.0 g.) in diethyl carbonate (80 ml.) was added to a stirred suspension of sodium hydride (15.4 g.; weighed as a 60% w/w dispersion in oil, but subsequently washed by decantation with light petroleum, b.p. 40°-60° C., to remove the oil) in diethyl carbonate (20 ml.). The mixture was stirred under reflux for 11/2 hours, and formed a thick suspension. This was cooled and treated with a small amount of methanol to destroy any remaining sodium hydride. Dilution with ether (400 ml.) gave a suspension from which the solid was filtered. This was suspended in ethanol (180 ml.) and brought to pH 3 by addition of hydrochloric acid. Water (600 ml.) was added, and the suspension was stirred for 30 minutes before the solid was collected by filtration, washed with water, and well drained. This solid [which comprised diethyl 1-(4-chlorobenzyl)-1,2-dihydro-2-oxoquinol-4-ylmalonate] was dissolved in ethanol (180 ml.), to which was added aqueous 40% w/v sodium hydroxide (20 ml.), and the mixture was heated under reflux for 4 hours. The cooled mixture was added to water (600 ml.) to give a solution which was brought to pH 3 by addition of concentrated hydrochloric acid. The resultant precipitate was collected by filtration, washed with water, drained, and crystallised from ethanol to give 1-(4-chlorobenzyl)-1,2-dihydro-2-oxoquinol-4-ylacetic acid, m.p. 208°-209° C., in 51% overall yield.

Workup

  1. washsubsequently washed by decantation with light petroleum, b.p. 40°-60° C.
  2. customto remove the oil) in diethyl carbonate (20 ml.)
  3. temperatureunder reflux for 11/2 hours
  4. customformed a thick suspension
  5. temperatureThis was cooled
  6. customto destroy any remaining sodium hydride
  7. customDilution with ether (400 ml.) gave a suspension from which the solid
  8. filtrationwas filtered
  9. additionbrought to pH 3 by addition of hydrochloric acid
  10. additionWater (600 ml.) was added
  11. stirringthe suspension was stirred for 30 minutes before the solid
  12. filtrationwas collected by filtration
  13. washwashed with water
  14. dissolutionThis solid [which comprised diethyl 1-(4-chlorobenzyl)-1,2-dihydro-2-oxoquinol-4-ylmalonate] was dissolved in ethanol (180 ml.), to which
  15. additionwas added aqueous 40%
  16. temperaturethe mixture was heated
  17. temperatureunder reflux for 4 hours
  18. additionThe cooled mixture was added to water (600 ml.)
  19. customto give a solution which
  20. filtrationThe resultant precipitate was collected by filtration
  21. washwashed with water
  22. customcrystallised from ethanol

Sources & evidence

ORD record
ord-aeda30f618014cdbbed0b4bedd44177f
Source dataset
uspto-grants-1980_02
Patent number
US04187310

Reaction notes

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