Acetoacetanilide is an organic compound with the formula CH₃C(O)CH₂C(O)NHC₆H₅. It is the acetoacetamide derivative of

aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...

. 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

pigment A pigment is a powder used to add or alter color or change visual appearance. Pigments are completely or nearly solubility, insoluble and reactivity (chemistry), chemically unreactive in water or another medium; in contrast, dyes are colored sub ...

s called arylide yellows, one example being Pigment Yellow 74.

Structure

Acetoacetanilide crystallizes as the keto-amide tautomer according to

X-ray crystallography X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...

. The molecules are linked by intermolecular

hydrogen bond In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, Covalent bond, covalently b ...

s, which allows the benzoyl ketone to rotate out of the plane of the amide. For the general case of ''substituted'' acetoanilides, substituents on the aryl ring affect the balance of intra- vs intermolecular hydrogen bonding. The situation is illustrated by the 2' vs. 3' vs. 4' fluoro-substituted acetoacetanilides.

Preparation and reactions

Acetoacetanilide is prepared by acetoacetylation of aniline using diketene. Many analogues have been prepared. To make the dyes, acetoacetanilides are coupled to

diazonium salt Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent, comp ...

s, " azo coupling".K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. AcetoacetylationWithDiketene

In the presence of

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

, acetoacetanilide dehydrates to give 4-methyl -2-quinolone.

Related compounds

* Acetoacetamide, {{chem2, CH3COCH2CONH2 * C₁₀H₁₁NO₂

References

Anilides