N-(2-furanylmethyl) 5-nitro-2-(3-chloro-5-pyridyloxy)benzamide → N-(2-furanylmethyl) 5-amino-2-(3-chloro-5-pyridyloxy)benzamide

HRID 1167664Notes

Reaction equation

HRID 1167664 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8](=[O:26])[C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[O:18][C:19]1[CH:20]=[C:21]([Cl:25])[CH:22]=[N:23][CH:24]=1>CO.[Ni]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8](=[O:26])[C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[O:18][C:19]1[CH:20]=[C:21]([Cl:25])[CH:22]=[N:23][CH:24]=1

Participants

4

Reactant 1

HCID 54136240N-(2-furanylmethyl) 5-nitro-2-(3-chloro-5-pyridyloxy)benzamide

Product 1

HCID 53712390N-(2-furanylmethyl) 5-amino-2-(3-chloro-5-pyridyloxy)benzamideYield 76%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a 0.08M solution of N-(2-furanylmethyl) 5-nitro-2-(3-chloro-5-pyridyloxy)benzamide (3.7 g, 10 mmol, prepared in Example 35.2) in MeOH was added a 50% aqueous slurry of Raney nickel (˜6 mL). Hydrogen was then bubbled through the resulting solution for one minute. The resulting mixture was stirred at ambient temperature under one atmosphere of hydrogen for 16 hr. The crude reaction mixture was filtered through a pad of Celite® and the filter cake was washed 3× with MeOH. NOTE: Raney nickel is pyrophoric and should always be kept wet with solvent during the filtration. The Raney nickel can be quenched by adding 6M aqueous HCl. The filtrate was concentrated in the presence of benzene to azeotropically remove water. The residue was purified by chromatography (1-3% MeOH in CH2Cl2) to yield 2.6 g (76%) of N-(2-furanylmethyl) 5-amino-2-(3-chloro-5-pyridyloxy)benzamide as a pale brown solid.

Workup

  1. customHydrogen was then bubbled through the resulting solution for one minute
  2. customThe crude reaction mixture
  3. filtrationwas filtered through a pad of Celite®
  4. washthe filter cake was washed 3× with MeOH
  5. filtrationshould always be kept wet with solvent during the filtration
  6. customThe Raney nickel can be quenched
  7. additionby adding 6M aqueous HCl
  8. concentrationThe filtrate was concentrated in the presence of benzene to azeotropically remove water
  9. customThe residue was purified by chromatography (1-3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-45b400661faa458ab5dcd7d9cc7a3327
Source dataset
uspto-grants-2003_09
Patent number
US06620827B2

Reaction notes

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