Potassium Hydroxide → HCID 178524696, compound

HRID 1942923Notes

Reaction equation

HRID 1942923 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][C:12]1[O:17][CH2:18][O:19][C:11]=1[CH:10]=2)=[O:5])C.[OH-].[K+]>C(O)C>[OH:16][C:15]1[C:14]2[C:9](=[CH:10][C:11]3[O:19][CH2:18][O:17][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 842571,3-Dioxolo[4,5-g]quinoline-7-carboxylic acid, 8-hydroxy-, ethyl ester

Product 1

HCID 178524696HCID 178524696, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Hydroxy-6,7-methylenedioxy-3-quinolinecarboxylic acid ethyl ester (45.0 g, 0.172 mol) was added to a solution of KOH (16.8 g, 0.258 mol) in ethanol (500 mL) and the mixture was heated to reflux with stirring for 20 hours. The reaction flask was then cooled and ethanol was evaporated under reduced pressure. Then 800 mL of water were added with stirring to fully dissolve the potassium salt, and the solution was filtered to remove any impurities. Concentrated HCl was added to bring the mixture to pH 1, and the free acid was filtered off and dried under vacuum, to give 33.9 g as a beige solid, in 84%; mp>300° C. (lit.221 mp>290° C.); 1H NMR (DMSO-d6) δ 6.27 (s, 2H), 7.30 (s, 1H), 7.55 (s, 1H), 8.72 (s, 1H); 13C NMR (DMSO-d6) δ 98.5, 101.8, 103.8, 107.9, 120.8, 137.9, 143.5, 148.1, 153.7, 167.4, 177.4.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction flask was then cooled
  4. customethanol was evaporated under reduced pressure
  5. additionThen 800 mL of water were added
  6. stirringwith stirring
  7. dissolutionto fully dissolve the potassium salt
  8. filtrationthe solution was filtered
  9. customto remove any impurities
  10. additionConcentrated HCl was added
  11. filtrationthe free acid was filtered off
  12. customdried under vacuum
  13. customto give 33.9 g as a beige solid

Sources & evidence

ORD record
ord-8220aa6273da45af869595947f987302
Source dataset
uspto-grants-2013_03
Patent number
US08389721B2

Reaction notes

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