Reaction #7589

Reaction equation

4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline

→

4-(2-fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline

Yield 46.5%

Solvents

methanol

DMF

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration
2. 2
   Otherthe solvent was evaporated
3. 3
   WashThe residue was washed with methanol and ether
4. 4
   Otherdried under vacuum

Procedure

A solution of 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline (242 mg 0.5 mmol) in a mixture of methanol (9 ml) and DMF (10.5 ml) containing 10% palladium-on-charcoal catalyst (100 mg) was stirred under hydrogen at 5 atmospheres pressure for 9 hours. The catalyst was removed by filtration and the solvent was evaporated. The residue was washed with methanol and ether and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline as a white solid (87 mg, 44%).

Source