3-PHENYLAZOACETYLACETONE synthesis
- Product Name:3-PHENYLAZOACETYLACETONE
- CAS Number:56276-49-4
- Molecular formula:C11H12N2O2
- Molecular Weight:204.23
Yield:56276-49-4 95%
Reaction Conditions:
Stage #1: anilinewith hydrogenchloride;sodium nitrite in water at 0 - 5; for 0.5 h;
Stage #2: acetylacetonewith ammonium acetate in ethanol;water at 0 - 5; pH=5 - 6;
Steps:
A.A-1.a
A. Starting materials; A-I: 3-((E)-3-Dimethylamino-acryloyl)-l-phenγl-lH-pyridazin-4-one; a) 3-Phenylazo-pentane-2,4-dione; A solution of aniline (5.0 g, 54 mmol) in IN HCl (100 ml) is cooled to 0-5 0C and reacted with a solution of sodium nitrite (3.89 g, 56 mmol) in H2O (sulfination flask with mechanic stirrer). Stirring is continued for 30 min at 0-5 0C (suspension of diazonium salt). In parallel, a solution of 2,4-pentadione (6.7 g ; 67 mmol) in EtOH (15 ml) and water (250 ml) is prepared and cooled to 0-5 0C. The pentadione solution is added to the suspension of the diazonium salt while vigorously stirring. After completion, NH4OAc is added until the pH reaches 5-6. The creamy yellow suspension is stirred for another 3 h at the same temperature. The solid material is filtered, washed with water, transferred into a flask and dried. Residual water can be removed with either ethyl acetate or acetone (in this case better) yielding 10.4 g (95 %) of the desired product.DC: Rf = 0.4 (EE/heptane = 1:3)
References:
WO2010/63610,2010,A1 Location in patent:Page/Page column 48
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