Hydrochloric Acid → 1,2-Dihydro-4-(3,4-methylenedioxyphenyl)-2-oxo-3-quinoline carboxylic acid

HRID 3148Notes

Reaction equation

HRID 3148 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:25])[NH:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]3[O:22][CH2:23][O:24][C:18]=3[CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])C.CO.[OH-].[K+].Cl>O>[CH2:23]1[O:22][C:19]2[CH:20]=[CH:21][C:16]([C:15]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[NH:8][C:7](=[O:25])[C:6]=3[C:4]([OH:5])=[O:3])=[CH:17][C:18]=2[O:24]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 539206231,2-Dihydro-4-(3,4-methylenedioxyphenyl)-2-oxo-3-quinoline carboxylic acid ethyl ester

Product 1

HCID 193561261,2-Dihydro-4-(3,4-methylenedioxyphenyl)-2-oxo-3-quinoline carboxylic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,2-dihydro-4-(3,4-methylenedioxyphenyl)-2-oxo-3-quinoline carboxylic acid ethyl ester (40 g, 118.6 mmol), methanol (200 ml), water (300 ml) and potassium hydroxide (33.3 g, 593.5 mmol) was refluxed with heat for 40 hours. To the reaction mixture was added 110 ml of 6N-HCl to acidify the mixture to obtain a precipitated crystal by filtration. The crystal obtained was washed with diethylether to give 35 g (yield: 95.4%) of the title compound.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heat for 40 hours
  3. customto obtain a precipitated crystal
  4. filtrationby filtration
  5. customThe crystal obtained
  6. washwas washed with diethylether

Sources & evidence

ORD record
ord-18f7f5d0bdf24923973a1222b73ecdad
Source dataset
uspto-grants-1998_03
Patent number
US05733918

Reaction notes

Loading…