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Ammonolysis of 3‐hydroxypicolinic acids. A correction and illustration of the use of 13 C Nmr OH/OD isotope shifts
Author(s) -
Moore George G. I.,
Kirk Alan R.,
Newmark Richard A.
Publication year - 1979
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.5570160436
Subject(s) - chemistry , ammonia , isotope , chemical shift , liquid ammonia , carbon 13 nmr , organic chemistry , medicinal chemistry , physics , quantum mechanics
Ammonolysis of 3‐hydroxy‐6‐methylpicolinic acid ( 1a ) has been reported to give 3‐amino‐6‐methylpicolinic acid. However, on heating 3‐hydroxypicolinic acid with ammonia at 200°, the product proved to be the known 3‐hydroxypicolinamide. 13 C Nmr OH/OD isotope shifts in DMSO show that ammonolysis of 1a gives not 2a , but instead 3‐hydroxy‐6‐methylpicolinamide.