1-METHYL-1H-INDAZOL-5-AMINE synthesis
- Product Name:1-METHYL-1H-INDAZOL-5-AMINE
- CAS Number:50593-24-3
- Molecular formula:C8H9N3
- Molecular Weight:147.18
5228-49-9
50593-24-3
Step 2: Preparation of 1-methyl-1H-indazol-5-amine Iron powder (5.04 g, 90.3 mmol) was added batchwise to a mixed solution of ethanol (225 mL) and water (100 mL) of 1-methyl-5-nitro-1H-indazole (4.00 g, 22.6 mmol), followed by ammonium chloride (12.1 g, 225 mmol). The reaction mixture was stirred and heated at 80 °C for 1 hour. After completion of the reaction, the reaction mixture was diluted with dichloromethane (500 mL) and filtered to remove insoluble material. The organic layer was separated, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound 1-methyl-1H-indazol-5-amine (3.29 g, 99% yield). HPLC analytical conditions: SYMMETRY C18 column (3.5 μm, 4.6 × 30 mm); mobile phase: acetonitrile/water gradient containing 0.1% trifluoroacetic acid (2%-98% acetonitrile, 10 min); flow rate: 2 mL/min; retention time: 1.06 min. Mass spectrum (MS): m/z 147.2 ([M+H]+).
5228-49-9
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50593-24-3
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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
5401-94-5
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$14.00/5g
50593-24-3
124 suppliers
$8.00/250mg