2-(3,4-Dimethoxyphenyl)-5-nitropyridine → 6-(3,4-Dimethoxy-phenyl)-pyridin-3-ylamine

HRID 445788Notes

Reaction equation

HRID 445788 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>CO.C1COCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 1

HCID 447849122-(3,4-Dimethoxyphenyl)-5-nitropyridine

Product 1

HCID 596196446-(3,4-Dimethoxy-phenyl)-pyridin-3-ylamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(3,4-dimethoxyphenyl)-5-nitropyridine (Interchim, Montlucon, France, 2.85 g, 10.95 mmol) in MeOH (27 ml) and THF (27 ml), Ra/Ni catalyst (1.10 g, 10.95 mmol) was added and shaked under hydrogen at rt for 15 h. After that, the RM was filtered over celite, the catalyst was washed with MeOH and the filtrate was evaporated to dryness to give the title compound as an off-white solid. (HPLC: tR 2.22 min (Method A); M+H=231 MS-ES)

Workup

  1. additionwas added
  2. filtrationAfter that, the RM was filtered over celite
  3. washthe catalyst was washed with MeOH
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-3128a27f1bdd44d89d671bad8cd2834a
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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