反应 #1880986

反应方程式

sodium perborate tetrahydrate

3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-6-amine

→

6-Nitro-3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

收率 103.6%

amber oil

收率 103.6%

溶剂

acetic acid

acetic acid

反应条件

后处理

1. 1
   温度heated to 50–60° C.
2. 2
   其他over 30 min
3. 3
   过滤The mixture was filtered
4. 4
   其他partitioned between CH2Cl2 and water
5. 5
   洗涤The organic layer is washed with water
6. 6
   浓缩concentrated

实验过程

Under N2, a flame-dried, 100-mL, three-necked flask is charged with sodium perborate tetrahydrate (5.75 g, 37.4 mmol) and acetic acid (20 mL) and heated to 50–60° C. using an oil bath. A solution of 3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-6-amine (1.93 g, 7.5 mmol) in acetic acid (20 mL) was slowly added drop-wise over 30 min. The mixture is heated at 55° C. for 1 hour. The mixture was filtered and partitioned between CH2Cl2 and water. The organic layer is washed with water and concentrated to give 2.24 g of an amber oil. Column chromatography (elution with 10–25% EtOAc/heptane) gives 1.52 g (70%) of the title compound as a yellow oil. An analytical sample was crystallized from EtOAc/hexane to give off-white crystals: mp 64–67° C.; 1H NMR (400 MHz, CDCl3) δ 7.63 (d, J=8 Hz, 1 H), 7.41–7.29 (m, 2 H), 3.89–3.74 (m, 4 H), 3.15–3.10 (m, 4 H); IR (diffuse reflectance) 1687, 1523, 1466, 1451, 1376, 1368, 1295, 1197, 1186, 1179, 1168, 1147, 950, 818, 752 cm−1; MS (EI) m/z 288 (M+); Anal. Calcd for C12H11F3N2O3: C, 50.01; H, 3.85; N, 9.72; F, 19.77. Found: C, 49.95; H, 3.88; N, 9.68.

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