Tetrahydrofuran → 8-Cyclopropyl-4-methoxyquinoline-2-carboxylic acid

HRID 545218Notes

Reaction equation

HRID 545218 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[C:11]([C:14]([O:16]C)=[O:15])[CH:10]=[C:9]3[O:18][CH3:19])[CH2:3][CH2:2]1.C1COCC1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[C:11]([C:14]([OH:16])=[O:15])[CH:10]=[C:9]3[O:18][CH3:19])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57440912Methyl 8-cyclopropyl-4-methoxyquinoline-2-carboxylate

Product 1

HCID 574408908-Cyclopropyl-4-methoxyquinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

30.0 g of methyl 8-cyclopropyl-4-methoxyquinoline-2-carboxylate, 250 ml of THF and 400 ml of MeOH was placed in 2 L-flask, and 46 ml of 5N NaOH aq. was added, and stirred for 1 h. The mixture was concentrated in vacuo and diluted with water. 46 ml of 5N HCl aq. was added with cooling in ice bath, extracted with 500 ml of CHCl3-MeOH (4-1), dried over Na2SO4 and filtered. The filtrate was concentrated to afford a yellow solid. The solid was washed with hexane-CHCl3, filtered and dried under vacuum to afford 8-cyclopropyl-4-methoxyquinoline-2-carboxylic acid.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with water
  4. addition46 ml of 5N HCl aq. was added
  5. temperaturewith cooling in ice bath
  6. extractionextracted with 500 ml of CHCl3-MeOH (4-1)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customto afford a yellow solid
  11. washThe solid was washed with hexane-CHCl3
  12. filtrationfiltered
  13. customdried under vacuum

Sources & evidence

ORD record
ord-b43a57832c0e49139d68137ad3b9822b
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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