HCID 21875753, compound → HCID 21875783, compound

HRID 858404Notes

Reaction equation

HRID 858404 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=2)[C:5]([N+:18]([O-])=O)=[CH:4][CH:3]=1>CO.[Pd]>[NH2:18][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=2)=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 21875753HCID 21875753, compound

Product 1

HCID 21875783HCID 21875783, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-{4-[(6-methyl-3-nitro-2-pyridinyl)amino]phenyl}ethanol (step 1, 4.6 g, 16.9 mmol) in methanol (100 mL) was added 10% Pd—C (300 mg). The resulting mixture was stirred for 2 h under hydrogen atmosphere. The mixture was filtered through a pad of Celite and the filtrate was concentrated. The residue was purified by flash column chromatography eluting with hexane/ethyl acetate (gradient elution from 1:2 to 1:5) to afford 3.8 g (92%) of the title compound as yellow solids: 1H-NMR (CDCl3) δ: 7.10–7.16 (4H, m), 6.91 (1H, d, J=8.4 Hz), 6.70 (1H, d, J=8.4 Hz), 6.19 (1H, s), 3.83 (2H, t, J=6.4 Hz), 2.81 (2H, t, J=6.4 Hz), 2.35 (3H, s).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash column chromatography
  4. washeluting with hexane/ethyl acetate (gradient elution from 1:2 to 1:5)

Sources & evidence

ORD record
ord-d01d486fd8064588825150cc30b0860c
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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