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Encyclopedia Britannica



CINNOLIN, CRH6N2

This article appears in Volume V06, Page 377 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: CHR-CLI
CINNOLIN, CRH6N2 , a compound isomeric with phthalazine, prepared by boiling dihydrocinnolin dissolved in benzene with freshly precipitated mercuric
oxide
 . The solution is filtered and the hydrochloride of the base precipitated by alcoholic hydrochloric acid; the free base is obtained as an oil by adding
caustic
  soda. It may be obtained in white silky needles, melting at 24-25 C. and containing a molecule of ether of crystallization by cooling the oil dissolved in ether. The free base melts at 39 C. It is a strong base, forming stable salts with
mineral
  acids, and is easily soluble in water and in the
ordinary
  organic solvents. It has a
taste
  resembling that of chloral hydrate, and leaves a
sharp
  irritation for some time on the tongue; it is also very poisonous (M.
Busch
  and A. Rast, Berichte, 1897, 30, p. 521). Cinnolin derivatives are obtained from oxycinnolin carboxylic acid, which is formed by digesting orthophenyl propiolic acid diazo chloride with water. Oxycinnolin carboxylic acid on
heating
  gives oxycinnolin, melting at 2250, which with phosphorus pentachloride gives chlorcinnolin. This substance is reduced by iron filings and sulphuric acid to dihydrocinnolin.
The relations of these compounds are here shown:
cans C-OH /CH
' /NsNa f~ N N
C.COOH
O-phenyl propiolic Oxycinnolin Oxycinnolin amain
acid diazo hydroxide carboxylic acid


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