Formamidine acetate → HCID 178487763, compound

HRID 1811049Notes

Reaction equation

HRID 1811049 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(O)(=O)C.[CH:17](N)=[NH:18]>COCCO>[CH3:12][O:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4]([OH:5])=[N:18][CH:17]=[N:1]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 3510102-Amino-4-methoxybenzoic acid

Product 1

HCID 178487763HCID 178487763, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
130 °C

Procedure

Step 1 A mixture of 2-amino-4-methoxybenzoic acid (0.5 g, 2.99 mmol) and formamidine acetate (0.623 g, 5.98 mmol) in 2-methoxyethanol (4 mL) was heated at 130° C. After 15.25 h, the mixture was cooled to rt. The resulting precipitate was collected by filtration, washed with methanol and dried to provide 7-methoxyquinazolin-4-ol as a tan solid (473 mg, 90%). 1H NMR (400 MHz, DMSO-d6) δ 12.08 (1 H, br. s.), 8.06 (1 H, s), 8.03 (1 H, d, J=9.5 Hz), 7.03-7.14 (2 H, m), 3.90 (3 H, s).

Workup

  1. temperaturethe mixture was cooled to rt
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-dbb7e3abeda4448e845102690cab76c6
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

Loading…