Formamide → 6-fluoroquinazolin-4-ol

HRID 618673Notes

Reaction equation

HRID 618673 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4](O)=[O:5].[CH:12]([NH2:14])=O>O>[F:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[CH:12][NH:14][C:4]2=[O:5]

Participants

4

Reactant 2

HCID 713FormamideHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 1354805206-fluoroquinazolin-4-olYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-amino-5-fluorobenzoic acid (2.07 g) and formamide (4 ml) was heated at 160° C. for 2 hours, and for a further 2 hours at 180° C. The reaction mixture was allowed to cool and water was added. The reaction product was filtered off and washed with water and with diethyl ether to give 6-fluoro-3,4-dihydroquinazolin-4-one in 78% yield: m.p. 269-271° C.;

Workup

  1. temperatureto cool
  2. filtrationThe reaction product was filtered off
  3. washwashed with water and with diethyl ether

Sources & evidence

ORD record
ord-96f8fe7d8f014eac950a779a1e1b6ec4
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

Loading…