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

HRID 1882923Notes

Reaction equation

HRID 1882923 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 62601Nickel acetate tetrahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0d27dd0e9a2148d9841a3d4206b39f26
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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