Hydrochloric Acid → 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid

HRID 387757Notes

Reaction equation

HRID 387757 reaction equation
OCC(CO)O.[OH-:7].[K+].[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:21])[CH:16]=[CH:17][NH:18]2)=[CH:13][C:12]=1[C:22]#N.Cl.[OH2:25]>>[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:21])[CH:16]=[CH:17][NH:18]2)=[CH:13][C:12]=1[C:22]([OH:25])=[O:7]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 753GlycerolHCID 962WaterHCID 14797Potassium HydroxideHCID 229363917-Methoxy-4-oxo-1,4-dihydroquinoline-6-carbonitrile

Product 1

HCID 229364397-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid

Conditions

Temperature
160 °C

Procedure

Glycerol (20 ml) and potassium hydroxide (KOH, 3.0 g) were added to the 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carbonitrile (2 g) of Production Example 24, and after heating and stirring at 160° C. for 3 hours, water (40 ml) was added and the mixture was heated at 80° C. for 30 minutes. After cooling, 2N hydrochloric acid was added to acidity and the precipitated insoluble portion was filtered out, washed with water and then dried under reduced pressure to obtain the title compound (1.6 g).

Workup

  1. temperatureafter heating
  2. temperaturethe mixture was heated at 80° C. for 30 minutes
  3. temperatureAfter cooling
  4. filtrationthe precipitated insoluble portion was filtered out
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-778ff924cc67439b98cc979ce09b04b3
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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