Acetoacetanilide
Acetoacetanilide is an organic compound with the formula CH3CCH2CNHC6H5. It is the acetoacetamide derivative of aniline. It is a white solid that is poorly soluble in water. This chemical and many related compounds are used in the production of organic pigments called arylide yellows, one example being Pigment Yellow 74.
Structure
Acetoacetanilide crystallizes as the keto-amide tautomer according to X-ray crystallography. The molecules are linked by intermolecular hydrogen bonds, 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 salts, "azo coupling".
In the presence of sulfuric acid, acetoacetanilide dehydrates to give 4-methyl-2-quinolone.