Organic Medicinal Chemicals Synthetic And Natural

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A modification of the above method of resolving racemic adrenaline is given in D. R. P. 269327. R- adrenaline, 182 VASOCONSTRICTORS AND VASO-DILATORS 221 parts, is dissolved, together with 150 parts of dextro-tartaric acid, in 1000 parts of hot methyl alcohol. L, sevo-adrenaline d-tartrate crystallises out on cooling, and, after several days' standing, is filtered off and purified by being twice recrystal- lised from methyl alcohol.
Other methods of preparing r-adrenaline are : (i) Diacetyl-pro
...to-catechuic aldehyde (I) on condensa- tion with nitro-methane in feebly alkaline aqueous solution yields j8-hydroxyrj8-3 : 4-diacetoxy-phenyl-nitro-ethane (II). When this is mixed with the calculated quantity of formalde- hyde and reduced by zinc and acetic acid, j8-hydroxy-j3- 3 : 4-diacetoxy-phenyl-ethyl-methylamine (III) is formed, from which adrenaline is obtained on removal of the acetyl groups.
OAc OAc OAc AOAC ^ AOAC ^ \y \/.
CHO CH(OH)-CH 2 -NOo CH(OH)'CH 2 'NHMe (I) (II) ' (III) (N. Nagai, Jap.


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