Acetic Acid → 2-Amino-4-pyridin-3-YL-phenol

HRID 393535Notes

Reaction equation

HRID 393535 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][C:5]=1[OH:16])([O-])=O.C(O)(=O)C>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][C:5]=1[OH:16]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 6122253-(4-Hydroxy-3-nitrophenyl)pyridine

Product 1

HCID 224958092-Amino-4-pyridin-3-YL-phenolYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-nitro-4-pyridin-3-yl-phenol (80 mg, 0.37 mmol), 10% Pd-C (8.0 mg), acetic acid (21 μL, 0.37 mmol) in MeOH (3.7 mL) was hydrogenated at 45 PSI at RT for 16 h. The mixture was filtered through a pad of celite and concentrate to afford 70 mg (100%) of the title compound as a brown oil: 1H NMR (CDCl3, 400 MHz) δ 8.57 (d, 1H, J=1.7 Hz), 8.30 (d, 1H, J=5.0 Hz), 7.75 (dt, 1H, J=7.9, 2.1 Hz), 7.25 (dd, 1H, J=7.9, 5.0 Hz), 6.77-6.69 (m, 2H), 3.94 (br s, 3H); 13C NMR (CDCl3, 100 MHz) δ 147.0, 146.5, 145.7, 137.6, 135.5, 134.8, 129.3, 124.0, 118.1, 115.4, 114.6; MS (Cl) m/z 187.1 (M+1); HPLC retention time=1.29 min.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-7335172fc66247bda0c4ddac3cc84848
Source dataset
uspto-grants-2004_10
Patent number
US06809094B2

Reaction notes

Loading…