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Paper | Regular issue | Vol 31, No. 7, 1990, pp.1301-1308
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5401
Reaction of β-Bromo-N-heteroaromatics with Phenylacetonitrile

Setsuya Ohba, Takao Sakamoto, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

The reaction of 3-bromopyridine with phenylacetonitrile in the presence of NaH in THF gave a simple substitution product, α-phenyl-3-pyridineacetonitrile, whereas the reaction of 5-bromopyrimidine with phenylacetonitrile under similar conditions gave a ring-transformation product, 2-amino-5-bromo-3-phenylpyridine. 3-Bromoquinoline and 4-bromoisoquinoline underwent the former type reaction, while 3-bromo- and 3-chloroisoquinolines were converted into 2-amino-3-phenyl-1-naphthalenecarbonitrile according to the latter type reaction.