反応 #959455

反応方程式

Sodium nitrite

1-(cyclobutylmethyl)-1H-benzotriazol-5-amine

→

1-(cyclobutylmethyl)-1H-benzotriazol-5-ol

溶媒

sulfuric acid

反応条件

後処理

1. 1
   その他the resulting mixture was irradiated at 120° C. in a microwave reactor for 40 min
2. 2
   その他partitioned between water (300 mL) and ethyl acetate (2×100 mL)
3. 3
   乾燥The combined organic layers were dried over sodium sulfate
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The residue was purified by silica gel chromatography (hexanes, grading to 100% ethyl acetate)

実験手順

Sodium nitrite (61 mg, 0.89 mmol, 1.2 equiv) was added to a solution of 1-(cyclobutylmethyl)-1H-benzotriazol-5-amine (3-3, 150 mg, 0.74 mmol, 1 equiv) in 20% aqueous sulfuric acid solution (5 mL) and the resulting mixture was irradiated at 120° C. in a microwave reactor for 40 min. The reaction mixture was cooled to ambient temperature and then partitioned between water (300 mL) and ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (hexanes, grading to 100% ethyl acetate) to give 1-(cyclobutylmethyl)-1H-benzotriazol-5-ol (3-4) as a light yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.45 (d, 1H, J=2.1 Hz), 7.42 (d, 1H, J=8.9 Hz), 7.16 (dd, 1H, J=8.9, 2.1 Hz), 6.39 (br s, 1H), 4.61 (d, 2H, J=7.3 Hz), 2.99 (p, 1H, J=7.6 Hz), 2.08 (m, 2H), 1.91 (m, 4H) ppm. LRMS m/z (M+H) 204.0 found, 204.1 required.

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