Reaction #84070

Reaction equation

N-hydroxy-4-(6-hydroxyquinolin-2-yl)benzimidamide

CDI

→

Compound 12

Yield 36.1%

3-(4-(6-hydroxyquinolin-2-yl)phenyl)-1,2,4-oxadiazol-5(2H)-one

Yield 36.1%

Solvents

THF

Conditions

Workup

1. 1
   Concentrationfollowed by concentration in vacuo
2. 2
   workup.DISSOLUTIONThe crude material was dissolved in 10 mL 1N NaOH
3. 3
   Filtrationfiltered through celite
4. 4
   Filtrationthe solids were filtered
5. 5
   Otherdried
6. 6
   workup.WAITThe solids were slurried in 10 mL of EtOAc overnight at 50° C.
7. 7
   Filtrationfollowed by filtration

Procedure

N-hydroxy-4-(6-hydroxyquinolin-2-yl)benzimidamide (800 mg, 2.86 mmol) was dissolved in 25 mL of THF and CDI (557 mg, 3.44 mmol) and TEA (0.2 mL) was added. The mixture was stirred at 65° C. for 2 hours, followed by concentration in vacuo. The crude material was dissolved in 10 mL 1N NaOH and filtered through celite. The mixture was then acidified with 1N HCl to a pH of 4.5 and the solids were filtered and dried. The solids were slurried in 10 mL of EtOAc overnight at 50° C. followed by filtration to yield Compound 12 (315 mg, 36% yield). 1H NMR (DMSO-d6, 400 MHz): δ 10.19 (s, 1H), 8.42 (d, 2H), 8.28 (d, 1H), 8.14-8.11 (d, 1H), 8.00-7.94 (m, 3H), 7.39-7.35 (dd, 1H), 7.21 (s, 1H). MS (ESI): m/z 306.44 [M+H]+.

Source