ChemicalBook CAS DataBase List 6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone synthesis

12synthesis methods

Product Name:6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
CAS Number:36725-28-7
Molecular formula:C11H13N3O
Molecular Weight:203.24

4-(4-aMinophenyl)-3-Methyl-4-oxobutanoic acid hydrochloride

120757-13-3

36725-28-7

General procedure for the synthesis of 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone from 4-(4-aminophenyl)-3-methyl-4-oxobutanoic acid hydrochloride: hydrazine hydrate (1.40 mL, 28.7 mmol) was added to an ethanolic solution of intermediate 3 (2.69 g, 11.04 mmol, dissolved in 70 mL of ethanol), the The reaction mixture was heated to reflux at 80 °C for 18 hours. After completion of the reaction, the mixture was concentrated in vacuum and the residue was ground with ethyl acetate to afford the target product Intermediate 7 in 1.46 g yield, 65%. The product was characterized by 1H NMR (300 MHz, CD3OD): δ [ppm] = 1.13 (d, 3H), 2.33 (d, 1H), 2.66 (dd, 1H), 3.28-3.40 (m, 1H), 6.68 (d, 2H), 7.56 (d, 2H). analysis by UPLC-MS (Method 3) showed a retention time R = 0.47 min and 100% purity. m/z (M + H)+ = 204 as measured by MS (ESIpos).

120757-13-3
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36725-28-7
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Yield:36725-28-7 65%

Reaction Conditions:

with hydrazine hydrate at 80; for 18 h;

Steps:

6-(4-aminophenyl)-5-methyl-4, 5-dihydropyridazin-3(2H )-one

To a solution of Intermediate 3, 2.69 g (11.04 minol), in ethanol, 70 mL, was added hydrazine hydrate, 1.40 mL (28.7 minol), the reaction was heated at 8000 for 18 hours. The reaction wasconcentrated under vacuum and triturated with ethyl acetate to give the desired product Intermediate 7, 1.46 g (65%).1H NMR (300 MHz, CD3OD): 6 [ppm] = 1.13 (d, 3H), 2.33 (d, IH), 2.66 (dd, IH), 3.28-3.40 (m, IH), 6.68 (d, 2H), 7.56 (d, 2H).UPLC-MS (Method 3): R = 0.47 min., 100%. MS (ESIpos): m/z (M÷H) 204.

References:

WO2018/86703,2018,A1 Location in patent:Page/Page column 204

101328-84-1 Synthesis