Hydrochloric Acid → 7-carboxy-1-isopropyl-4-(m-methoxyphenyl)-2(1H)-quinazolinone

HRID 1834763Notes

Reaction equation

HRID 1834763 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](C)[CH:12]=2)[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[N:6][C:5]1=[O:23])([CH3:3])[CH3:2].[C:24](=[O:27])([O-])[O-:25].[Na+].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].Cl.S([O-])([O-])(=O)=O.[Na+].[Na+]>[O-2].[O-2].[Mn+4].O>[C:24]([C:11]1[CH:12]=[C:13]2[C:8]([C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)=[N:6][C:5](=[O:23])[N:4]2[CH:1]([CH3:3])[CH3:2])=[CH:9][CH:10]=1)([OH:25])=[O:27]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 516875Potassium Permanganate2×HCID 46200211-isopropyl-7-methyl-4-(m-methoxyphenyl)-2(1H)-quinazolinone

Product 1

HCID 203719547-carboxy-1-isopropyl-4-(m-methoxyphenyl)-2(1H)-quinazolinone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 11.25 g. of 1-isopropyl-7-methyl-4-(m-methoxyphenyl)-2(1H)-quinazolinone, 5.25 g. of sodium carbonate and 750 ml. of water is refluxed with 7.5 g. of potassium permanganate being added every half hour until a total of 52.5 g. of potassium permanganate is added. After refluxing for an additional 45 minutes, the reaction mixture is cooled, acidified on the slow addition of 263 ml. of 6N. hydrochloric acid and then treated with sodium sulfate until the manganese dioxide is eliminated. The resulting mixture is cooled and filtered to recover the precipitate which is washed with water, dried under vacuum (40° C.) and crystallized from hot glacial acidic acid to obtain 7-carboxy-1--isopropyl-4-(m-methoxyphenyl)-2(1H)-quinazolinone.

Workup

  1. additionA mixture of 11.25 g
  2. temperatureAfter refluxing for an additional 45 minutes
  3. temperaturethe reaction mixture is cooled
  4. additionacidified on the slow addition of 263 ml
  5. temperatureThe resulting mixture is cooled
  6. filtrationfiltered
  7. customto recover the precipitate which
  8. washis washed with water
  9. customdried under vacuum (40° C.)
  10. customcrystallized from hot glacial acidic acid

Sources & evidence

ORD record
ord-6f76a33996e44893ae40eab844634f71
Source dataset
uspto-grants-1978_01
Patent number
US04071516

Reaction notes

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