Synthesis of 2‐[3′‐(trifluoromethyl)anilino] ‐5‐hydroxynicotinic acid | Zendy

Němec Josef | Zendy; Meeker Fred S. | Zendy; Schreiber Eric C. | Zendy

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Synthesis of 2‐[3′‐(trifluoromethyl)anilino] ‐5‐hydroxynicotinic acid

Author(s) -

Němec Josef,

Meeker Fred S.,

Schreiber Eric C.

Publication year - 1974

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.5570110422

Subject(s) - chemistry , trifluoromethyl , hydroxylation , stereochemistry , medicinal chemistry , organic chemistry , enzyme , alkyl

2‐[3′‐(Trifluoromethyl)anilino]‐5‐hydroxynicotinic acid (2) was synthesized by two routes: a) by direct hydroxylation of 2‐[3′‐(trifluoromethyl)anilino]nicotinie acid (1) ; and b) by the following sequence starting from 2‐chloro‐3‐methyl‐5‐nitropyridine (3) via 5‐amino‐2‐chloro‐3‐methylpyridine (4) , 2‐ehloro‐5‐hydroxy‐3‐methylpyridine (6) , 5‐acetoxy‐2‐chloro‐3‐methylpyridine (7) , 5‐acetoxy‐2‐chloronicotinie acid (8) , and 2‐chloro‐5‐hydroxynicotinic acid (9). The correlation of 2 with one of the metabolites of 1 has been accomplished, and the identities of both compounds have been proven.

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