Reaction #4387

Reaction equation

2-amino-3-hydroxypyridine

2-methylbenzyl chloride

→

2-amino-3-(2-methylbenzyloxy)pyridine

Solvents

sodium hydroxide

methylene chloride

Conditions

Workup

1. 1
   Otherthe organic layer was separated
2. 2
   Extractionthe aqueous layer was extracted with methylene chloride
3. 3
   WashThe combined extracts were washed with saturated sodium chloride aqueous solution
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Otherevaporated in vacuo
6. 6
   OtherThe crystalline residue was recrystallized from ethyl acetate

Procedure

To a mixture of 2-amino-3-hydroxypyridine (7 g) and Adogen 464 (Trademark: prepared by Aldrich Chemical Co.) (0.4 g) in 40% aqueous sodium hydroxide (32 ml) and methylene chloride (32 ml) was added 2-methylbenzyl chloride (8.42 ml) at ambient temperature. After being stirred for 24 hours, the organic layer was separated and the aqueous layer was extracted with methylene chloride. The combined extracts were washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was recrystallized from ethyl acetate to give 2-amino-3-(2-methylbenzyloxy)pyridine (7.56 g).

Source