Methylation and amination of folic acid | Zendy

Temple Carroll | Zendy; Kussner Conrad L. | Zendy; Montgomery John A. | Zendy

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Methylation and amination of folic acid

Author(s) -

Temple Carroll,

Kussner Conrad L.,

Montgomery John A.

Publication year - 1977

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570140532

Subject(s) - chemistry , hydroxylamine , methylation , methyl iodide , folic acid , amination , yield (engineering) , iodide , organic chemistry , base (topology) , sulfonic acid , medicinal chemistry , biochemistry , medicine , mathematical analysis , materials science , mathematics , metallurgy , gene , catalysis

The methylation of folic acid (2) with excess methyl iodide resulted in the formation of dimethyl 1,3‐dimethylfolate ( 4 ), whereas, methylation of dimethyl folate ( 3 ) with an equimolar amount of methyl iodide gave mainly dimethyl 3‐methylfolate ( 6 ). Both 4 and 6 underwent the Dimroth rearrangement in base to give the corresponding 2‐deamino‐2‐methyiamino folic acids 5 and 7, respectively. Amination of 2 with hydroxylamine‐ O ‐sulfonic acid in dilute base gave a low yield of 3‐amino folic acid (8), which underwent Dimroth rearrangement to give 2‐deamino‐2‐hydrazino folic acid (9) in an acidic, but not a basic, medium.

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