An Alternate Route to 2-Amino-3-nitro-5-bromo-4-picoline: Regioselective Pyridine Synthesis via 2-Nitramino-picoline Intermediate-Reference-Cited by-同舟云学术

An Alternate Route to 2-Amino-3-nitro-5-bromo-4-picoline: Regioselective Pyridine Synthesis via 2-Nitramino-picoline Intermediate

Published:2007-07-31 Issue:5 Volume:11 Page:885-888
ISSN:1083-6160
Container-title:Organic Process Research & Development
language:en
Short-container-title:Org. Process Res. Dev.

Author:

Bhattacharya Apurba¹,Purohit Vikram C.¹,Deshpande Prashant¹,Pullockaran Annie¹,Grosso John A.¹,DiMarco John D.¹,Gougoutas Jack Z.¹

Affiliation:

1. Department of Chemistry, Texas A&M University-Kingsville, Kingsville, Texas 78363, Department of Chemistry, Texas A&M University-College Station, Texas 77842, and Bristol-Myers Squibb Pharmaceutical Institute, 1 Squibb Drive, New Brunswick, New Jersey 08903, U.S.A.

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/op700114d

Reference21 articles.

1. For a patentedsynthesis of 2-amino-5-bromo-3-nitro-4-picoline (1) see: Igarashiet al.U.S. Patent 5,290,943, 1992, [EP0530524].The synthesis involves protectionof the amine function of 2-aminopicoline via N-acetylation followedby bromination of the resulting NH-acetyl derivative. Nitration andaqueous hydrolysis of the acetamido group produced the desired compound.

2. aPartial solubility of the product in water made the isolation evenmore difficult after the steam distillation.

3. Synthesis of nevirapine and its major metabolite

4. Studies on the preparation of 3,4-disubstituted 2-methoxypyridines

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