Acetic Acid → N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine

HRID 572187Notes

Reaction equation

HRID 572187 reaction equation
C(O)(=O)C.[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:25]([N+:26]([O-])=O)=[C:24]([CH3:29])[CH:23]=[CH:22][N:21]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1.[Zn]>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:25]([NH2:26])=[C:24]([CH3:29])[CH:23]=[CH:22][N:21]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 58577297N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine

Product 1

HCID 58577506N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamineYield 70%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of zinc (40.2 g), THF (50 ml) and acetic acid (100 ml) was added slowly a solution of N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine (13.75 g) in THF (150 ml), and the obtained mixture was stirred at room temperature for 30 min. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with 1 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) and recrystallized from hexane/ethyl acetate to give the title compound (8.77 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with 1 M aqueous sodium hydroxide solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-5255e91a25ce4e91b1675ac650228100
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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