Reaction #5327

Reaction equation

hydroxylamine hydrochloride

sodium methoxide

dimethyl sulfoxide

sodium

2'-cyano-4-methylbiphenyl

→

title compound

Methylbiphenyl-2-carboxamidoxime

Solvents

methanol

methanol

Conditions

Workup

1. 1
   workup.STIRRINGwas stirred for 5 hours at 100° C
2. 2
   OtherThe reaction mixture was partitioned between ethyl acetate and water
3. 3
   ExtractionThe aqueous layer was extracted with ethyl acetate
4. 4
   Washwashed with water
5. 5
   Otherdried
6. 6
   Otherthe solvent was evaporated in vacuo
7. 7
   OtherThe residue was purified by column chromatography on silica gel

Procedure

To a solution of hydroxylamine hydrochloride (17.9 g) in dimethyl sulfoxide (120 ml) was added a methanol solution of sodium methoxide prepared from metallic sodium (5.92 g) and anhydrous methanol (50 ml). The mixture was stirred for 10 minutes at room temperature, to which was added 2'-cyano-4-methylbiphenyl (10 g) The reaction mixture was stirred for 5 hours at 100° C. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. Organic layers were combined, washed with water and dried, then the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel to afford the title compound as a white amorphous product (11.2 g, 96%).

Source