海萝胶 → 4,5-Dibromo-2-(4-fluorophenyl)pyridazin-3(2H)-one

HRID 381901

反应方程式

HRID 381901 反应方程式
[C:1](O)(=O)/[C:2](=[C:4](\[CH:6]=[O:7])/[Br:5])/[Br:3].[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1.Cl>C(O)(=O)C>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:6](=[O:7])[C:4]([Br:5])=[C:2]([Br:3])[CH:1]=[N:18]2)=[CH:13][CH:12]=1

参与物

5

反应物 3

HCID 313海萝胶HCID 699824-氟苯肼HCID 3033972粘溴酸

产物 1

HCID 14768284,5-Dibromo-2-(4-fluorophenyl)pyridazin-3(2H)-one收率 86%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

反应条件

温度
115 °C

实验过程

Mucobromic acid (5.0 g, 19.4 mmol) dissolved in acetic acid (110 mL) was treated with 4-fluorophenyl hydrazine.HCl, and the heterogeneous mixture brought to reflux at a bath temperature of 115° C. for 15 hours. During the course of reaction, the mixture became a homogeneous deep red solution, and upon cooling to 23° C., a crystalline precipitate formed. The solution was poured into ice water (1000 mL) and stirred for 20 minutes. The yellow/brown crystals were filtered off, washed with additional cold water, and dried in vacuo to provide 5.8 g (86%) of product. (J. Het. Chem., 1993, 30, 1501; Heterocycles 1985, 23,2603) 1H NMR (300 MHz, DMSO-d6) δ 7.31-7.41 (m, 2H), 7.57-7.57-7.64 (m, 2H), 8.29 (s, 1H). MS (DCI+) m/z 347 (Br79Br79 M+H)+, m/z 349 (Br79Br81 M+H)+, m/z 364 (Br79Br79 M+NH4)+, and m/z 366 (Br79Br81 M+NH4)+.

后处理

  1. customDuring the course of reaction
  2. temperatureupon cooling to 23° C.
  3. customa crystalline precipitate formed
  4. filtrationThe yellow/brown crystals were filtered off
  5. washwashed with additional cold water
  6. customdried in vacuo

来源与证据

ORD记录
ord-36cee750e1ad44da883a4b2540beca21
来源数据集
uspto-grants-2001_10
专利号
US06307047B1

关联笔记

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