Hydrochloric Acid → Oxolinic acid

HRID 1658348Notes

Reaction equation

HRID 1658348 reaction equation
C([O:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]3[O:16][CH2:15][O:14][C:11]=3[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:17]([O:19]CC)=[O:18])C.[C:22]1(C)C=CC(S(O)(=O)=O)=C[CH:23]=1.[OH-].[Na+].Cl>>[CH2:22]([N:7]1[C:8]2[C:13](=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=2)[C:4](=[O:3])[C:5]([C:17]([OH:19])=[O:18])=[CH:6]1)[CH3:23]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 12367717Ethyl 8-ethoxy-2H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate

Product 1

HCID 4628Oxolinic acidYield 4,856.1%

Conditions

Temperature
180 °C

Procedure

A mixture of 5 g of ethyl 4-ethoxy-6,7-methylenedioxyquinoline-3-carboxylate and 0.06 g of p-toluene-sulfonic acid was heated at 180°C for 3 hours and cooled. To the product was added 50 ml of a 5% aqueous sodium hydroxide solution. The resulting mixture was heated at 90°-100°C for 30 minutes, the acidified by the addition of dilute hydrochloric acid and cooled. The precipitate was collected by filtration, washed with water and dried. There was obtained 4.42 g of 1-ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acid, m.p. 318°C (decomposition).

Workup

  1. temperaturecooled
  2. temperatureThe resulting mixture was heated at 90°-100°C for 30 minutes
  3. temperaturecooled
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2fdecf71a2944c4ca34233e06730d0c4
Source dataset
uspto-grants-1976_06
Patent number
US03963736

Reaction notes

Loading…