Condensation of 2-cyclohexanone-1-carboxylic acid anilide with ethyl cyanoacetate and cyanoacetamide was written by Bogdanowicz-Szwed, Krystyna. And the article was included in Roczniki Chemii in 1974.Application of 52903-71-6 The following contents are mentioned in the article:
2-Phenylcarbamoylcyclohexanone (I) and NCCH2CO2Et (II) refluxed in C6H6 in the presence of pyridine and piperidine (III) yielded 62% cyclohexene IV (R = 1-piperidinyl), which treated with H2SO4 at room temperature gave 53% isoquinoline V, and at 100° gave 75% VI. Under similar conditions, 2-phenylcarbamoyl-1-(4-morpholinyl)cyclohex-1-ene and II refluxed in the presence of pyridine and morpholine yielded 90% IV (R = 4-morpholinyl), which was converted into V and VI as above. VI refluxed with 20% NaOH gave 46% VII. Condensation of I with NCCH2CONH2 (VIII) in the presence of pyridine and III yielded 42% V; the same reactants condensed in the presence of AcOH-AcONa gave 58% IV (R = NH2) and small amounts of V. IV (R = NH2) with H2SO4 at room temperature gave 74% IX, but refluxing with 20% HCl in aqueous EtOH gave 82% X. X was also prepared from 2-carbethoxycyclohexanone and VIII. X hydrolyzed with H2SO4 at 100° yielded 45% XI, also prepared in 54% yield from IX. Both IX and X with aqueous NH3 gave the NH4 salt of X. This study involved multiple reactions and reactants, such as 1-Hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (cas: 52903-71-6Application of 52903-71-6).
1-Hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (cas: 52903-71-6) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. The Pomeranz–Fritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Application of 52903-71-6
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem