Acetoacetanilide Explained

Acetoacetanilide is an organic compound with the formula CH3C(O)CH2C(O)NHC6H5. It is the acetoacetamide derivative of aniline. It is a white solid that is poorly soluble in water. This chemical and many related compounds (prepared from various aniline derivatives) are used in the production of organic pigments called arylide yellows. Acetoacetanilides usually exist as the keto-amide tautomer according to X-ray crystallography.[1]

Preparation and reactions

Acetoacetanilide is prepared by acetoacetylation of aniline using diketene.[2] Many analogues have been prepared.[3]

To make the dyes, acetoacetanilides are coupled to diazonium salts, "azo coupling".[4]

In the presence of sulfuric acid, acetoacetanilide dehydrates to give 4-methyl-2-quinolone.[5]

See also

References

  1. 10.1021/ja000921+ . 2000 . 122 . 42 . Gilli . Paola . Bertolasi . Valerio . Ferretti . Valeria . Gilli . Gastone . Evidence for Intramolecular N−H···O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation . Journal of the American Chemical Society .
  2. 10.15227/orgsyn.021.0004 . Acetoacetanilide . Organic Syntheses . 1941 . 21 . 4. Jonathan W.. Williams. John A.. Krynitsky .
  3. Book: 10.1002/0471238961.151807011001060605.a01.pub2 . Pigments, Organic . Kirk-Othmer Encyclopedia of Chemical Technology . 2004 . Jaffe . Edward E. . 978-0-471-48494-3 .
  4. K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012.
  5. 10.15227/orgsyn.024.0068 . 4-Methylcarbostyril . Organic Syntheses . 1944 . 24 . 68. W. M.. Lauer. C. E.. Kaslow .

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