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ChemicalBook CAS DataBase List 1-METHYL-1H-INDAZOL-5-AMINE
50593-24-3

1-METHYL-1H-INDAZOL-5-AMINE synthesis

2synthesis methods
-

Yield: 99%

Reaction Conditions:

with iron;ammonium chloride in ethanol;water at 80; for 1 h;

Steps:

3.2
Step 2: Preparation of l-methyl-lH-indazol-5-amine Iron powder (5.04 g, 0.0903 mol) is added portionwise to a solution of l-methyl-5- nitro-lH-indazole (4.00 g, 0.0226 mol) and ammonium chloride (12.1 g, 0.225 mol) in ethanol (225 mL) and water (100 mL) at 8O0C. The mixture is stirred and heated for Ih, diluted with dichloromethane (500 mL) and filtered. The organic layer is separated, dried (Mg2SO4) and evaporated to afford the title compound (3.29 g, 99%); HPLC (SYMMETRY C18 3.5 μM, 4.6 x 30 mm column; gradient elution 2%-98% MeCN with 0.1% TFA over 10 min; 2 mL/min rate): retention time = 1.06 min; MS for C1OHnN3 m/z 147.2(M+H)+.

References:

PFIZER PRODUCTS INC. WO2007/88478, 2007, A1 Location in patent:Page/Page column 19

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