Acetic Acid → 6-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

HRID 1596275Notes

Reaction equation

HRID 1596275 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:8]([O:21][CH3:22])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:23]N(C=NC=[N+](C)C)C.[Cl-].C(O)(=O)C.C([O-])(=O)C.[Na+]>O1CCOCC1>[CH3:22][O:21][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[O:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[N:1]=[CH:23][NH:6][C:4]2=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 11008255Gold's ReagentHCID 216992712-Amino-5-methoxy-4-(3-morpholinopropoxy)benzamide

Product 1

HCID 1354371166-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-oneYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-5-methoxy4-(3-morpholinopropoxy)benzamide (4.57 g, 12.25 mmol) and Gold's reagent (2.6 g, 15.89 mmol) in dioxane (35 ml) was heated at reflux for 5 hours. Acetic acid (0.55 ml) and sodium acetate (1.0 g) were added to the reaction mixture which was heated for a further 3 hours. The mixture was cooled to ambient temperature and the volatiles removed by evaporation. The residue was adjusted to pH7 with 2 M sodium hydroxide and then purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with methanol (gradient of 0 to 60%) in water. Concentration of the fractions by evaporation gave a precipitate which was collected by filtration and dried under vacuum over phosphorus pentoxide to give 6-methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one (3.04 g, 78%) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. temperaturewas heated for a further 3 hours
  4. customthe volatiles removed by evaporation
  5. custompurified on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  6. washeluting with methanol (gradient of 0 to 60%) in water
  7. customConcentration of the fractions by evaporation
  8. customgave a precipitate which
  9. filtrationwas collected by filtration
  10. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-63f82ade9bc14359aa4e15e8c3048be7
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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