Formamidine acetate → HCID 178518022, compound

HRID 639967Notes

Reaction equation

HRID 639967 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].N[C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12]>COCCO>[F:18][C:16]1[CH:17]=[C:9]2[C:10]([C:11]([OH:12])=[N:6][CH:5]=[N:7]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 178518022HCID 178518022, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

Formamidine acetate (20.13 g, 193.4 mmol) was added to a solution of 2-amino-4-fluorobenzoic acid (15 g, 96.7 mmol) in 2-methoxyethanol (97 ml) and the mixture heated to reflux for 18 hours. The reaction was cooled, concentrated and the residue stirred in aqueous ammonium hydroxide (0.01 M, 250 ml) for 1 hour. The suspension was filtered, washed with water and dried over phosphorus pentoxide to yield 7-fluoroquinazolin-4-ol as an off-white solid (10.35 g, 65% yield):

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. filtrationThe suspension was filtered
  6. washwashed with water
  7. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-5cfad1d4e3a9456496e8e6b1c1f28561
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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