Sodium borohydride → N-(6-chloropyridin-3-yl)-2-aminobenzamide

HRID 988594

反応式

HRID 988594 の反応式
[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

参加物

6

反応物 2

HCID 4311764Sodium borohydrideHCID 21906170N-(6-chloropyridin-3-yl)-2-nitrobenzamide

生成物 1

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

試薬・触媒・溶媒 3

HCID 62601Nickel acetate tetrahydrate触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c6e66c3ee4ae4c0f9b234e448368404b
出典データセット
uspto-grants-2003_10
特許番号
US06635657B1

関連ノート

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