Acetic Acid → 6-methoxy-7-(3-morpholin-4-ylpropoxy)-1H-quinazolin-4-one

HRID 1597213Notes

Reaction equation

HRID 1597213 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>[OH:5][C:4]1[C:3]2[C:2](=[CH:10][C:9]([O:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:8]([O:21][CH3:22])[CH:7]=2)[N:1]=[CH:23][N:6]=1

Participants

6

Reactant 4

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

Product 1

HCID 1784867726-methoxy-7-(3-morpholin-4-ylpropoxy)-1H-quinazolin-4-oneYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-5-methoxy-4-(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 at reflux 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 2M 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 4-hydroxy-6-methoxy-7-(3-morpholinopropoxy)quinazoline (3.04 g, 78%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-b835628f4b6f4672afe9a85eaa743410
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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