硼氢化钠 → N-(6-chloropyridin-3-yl)-2-aminobenzamide

HRID 1247025

反应方程式

HRID 1247025 反应方程式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O1CCCC1.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[CH:4][CH:3]=1

参与物

6

反应物 2

HCID 4311764硼氢化钠HCID 21906170N-(6-chloropyridin-3-yl)-2-nitrobenzamide

产物 1

HCID 21906549N-(6-chloropyridin-3-yl)-2-aminobenzamide收率 46%

试剂、催化剂与溶剂 3

HCID 62601醋酸镍(四水)催化剂HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 8028四氢呋喃溶剂

实验过程

To a stirred solution of N-(6-chloropyridin-3-yl)-2-nitrobenzamide (0.6 g, 2.15 mmol) in methanol (150 mL) and tetrahydrofuran (75 mL) was added nickel acetate tetrahydrate (1.07 g, 4.3 mmol). Sodium borohydride (0.326 g, 8.61 mmol) was then added in small portions. After gas evolution had ceased, the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and concentrated ammonium hydroxide, and the layers separated. The organic phase was washed with concentrated ammonium hydroxide and saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated in vacuo. The solid was suspended in ether, sonicated, and filtered to give 0.243 g (46%) of a pink solid.

后处理

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and concentrated ammonium hydroxide
  3. customthe layers separated
  4. washThe organic phase was washed with concentrated ammonium hydroxide and saturated aqueous sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customsonicated
  9. filtrationfiltered

来源与证据

ORD记录
ord-4a5526ea2a04459ab92705179946e3b2
来源数据集
uspto-grants-2006_10
专利号
US07129245B2

关联笔记

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