Gould–Jacobs reaction

From Wikipedia, the free encyclopedia
  (Redirected from Gould-Jacobs reaction)
Jump to: navigation, search

The Gould–Jacobs reaction is an organic synthesis for the preparation of quinolines (more specifically, a 4-Quinolinol).[1] In this reaction aniline or an aniline derivative first reacts with malonic acid derivative ethyl ethoxymethylenemalonate with substitution of the ethoxy group by nitrogen. A benzannulation takes place by application of heat to a quinoline. The ester group is hydrolysed by sodium hydroxide to the carboxylic acid and decarboxylation again by application of heat to 4-hydroxyquinoline.

Gould-Jacobs reaction

Further reading:[2][3][4]


An example is the synthesis of 4,7-dichloroquinoline [5]


  1. ^ The Synthesis of Certain Substituted Quinolines and 5,6-Benzoquinolines R. Gordon Gould, , Walter Abraham Jacobs J. Am. Chem. Soc.; 1939; 61(10); 2890-2895. doi:10.1021/ja01265a088
  2. ^ Li, Jie Jack (2009). "Gould–Jacobs reaction": 263–265. doi:10.1007/978-3-642-01053-8_113. 
  3. ^ Lengyel, László Csaba; Sipos, Gellért; Sipőcz, Tamás; Vágó, Teréz; Dormán, György; Gerencsér, János; Makara, Gergely; Darvas, Ferenc (2015). "Synthesis of Condensed Heterocycles by the Gould–Jacobs Reaction in a Novel Three-Mode Pyrolysis Reactor". Organic Process Research & Development. 19 (3): 399–409. ISSN 1083-6160. doi:10.1021/op500354z. 
  4. ^ "Gould-Jacobs Reaction". 2010. doi:10.1002/9780470638859.conrr276. 
  5. ^ Organic Syntheses, Coll. Vol. 3, p.272 (1955); Vol. 28, p.38 (1948). Link