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

HRID 726677Notes

Reaction equation

HRID 726677 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-9408e060fdd4477992981376be720ec8
Source dataset
uspto-grants-1998_01
Patent number
US05710162

Reaction notes

Loading…