N -Methyl-3,4-dihydroxyphenylalaNINE

Ether cleavage. Deulofeu and Guerrero used the combination HI-P-Ac O in the last step of the preparation of N-methyl-3,4-dihydroxyphenylalanine. 

In a synthesis of N-methyl-3,4-dihydroxyphenylalanine (6) from vanillin (1) and creatinine (2), one step is a sodium amalgam reduction of (3)— (4), earned out by adding 3% amalgam in portions to a stirred suspension of (3) in water. The solid dissolves, and the initial orange-red color of the solution slowly fades as the reduction proceeds. With good agitation, decolorization is complete in 45-60 min. 

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