1-Methyl-6-nitro-1H-benzotriazole synthesis

4synthesis methods

Product Name:1-Methyl-6-nitro-1H-benzotriazole
CAS Number:25877-35-4
Molecular formula:C7H6N4O2
Molecular Weight:178.15

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Yield:25877-35-4 94%

Reaction Conditions:

with hydrogenchloride;sodium nitrite in water at -5 - 20; for 12 h;

Steps:

MC825_SC16.2-IS08115-084 Step 2-IS08115-084 1 -Methyl-6-nitro-1 H-benzotriazole

Step 2-IS08115-084 1 -Methyl-6-nitro-1 H-benzotriazole Procedure: To a solution of N2-methy[-4-nitro-benzene-1,2-diamine (1 g, 6 mmol) in aqueous HCI (5M, 20 mL) at -5 °C, an aqueous solution of sodium nitrite (0.82 g, 11.9 mmol) is added dropwise slowly and the reaction mixture is allowed to reach RT and stirred for 12 h. After completion of the reaction (monitored by TLC), the reaction mixture is basified with an aqueous solution of ammonium hydroxide (25%) to pH 8. The reaction mixture is extracted with ethylacetate (50 mL), washed with water (2 50mL), brine, dried over MgSO₄ and concentrated to get the product. Yield: 94 % (1 g, reddish brown solid). LCMS: (Method A) 179.0 (M+H), RT. 2.4 min, 98.0 % (Max), 98.4 % (254 nm). ¹H NMR (400 MHz, DMSO-d₆): δ [ppm] 8.98 (d, J = 2.0 Hz, 1H), 8.28 (d, J = 9.0 Hz, 1H), 8.22-8.19 (m, 1H), 4.45 (s, 3H).

References:

WO2013/124026,2013,A1 Location in patent:Page/Page column 113; 114