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

HRID 1247025

반응식

HRID 1247025 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 62601Nickel acetate tetrahydrate촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4a5526ea2a04459ab92705179946e3b2
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129245B2

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