Formamidine acetate → 6-Methoxyquinazolin-4-OL

HRID 1042865Notes

Reaction equation

HRID 1042865 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].N[C:9]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:10]=1[C:11](O)=[O:12]>COC(O)C>[CH3:19][O:18][C:15]1[CH:14]=[C:10]2[C:9](=[CH:17][CH:16]=1)[N:7]=[CH:5][NH:6][C:11]2=[O:12]

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 2779305-Methoxyanthranilic acid

Product 1

HCID 1354514236-Methoxyquinazolin-4-OL

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
140 °C

Procedure

Formamidine acetate (12.5 g, 119.6 mmol) was added to a stirred solution of 2-amino-5-methoxybenzoic acid (2.0 g, 119.6 mmol) in methoxy ethanol (40 mL) at RT. The reaction mixture was stirred at 140° C. (T oil bath) for ˜17 h. LC/MS showed completion of the reaction. The reaction cooled to RT and concentrated in vacuo. Aq. NaHCO3 solution was added to the concentrate and the precipitated solids were filtered (rinsing with water) to afford 6-methoxyquinazolin-4(3H)-one as off-white solid. MS [M+H]=177.1; Calc'd for C9H8N2O2: 176.2.

Workup

  1. customcompletion of the reaction
  2. temperatureThe reaction cooled to RT
  3. concentrationconcentrated in vacuo
  4. additionAq. NaHCO3 solution was added to the
  5. concentrationconcentrate
  6. filtrationthe precipitated solids were filtered
  7. wash(rinsing with water)

Sources & evidence

ORD record
ord-927d07b48ad4456f94a0ac55ca14224d
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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