Ammonium Acetate → 4-((6-Methylpyridin-3-yl)methoxy)pyridin-2(1H)-one

HRID 1918488Notes

Reaction equation

HRID 1918488 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[CH:5]=[CH:4][N:3]=1.C([O-])(=[O:19])C.[NH4+]>C(O)=O.O>[CH3:16][C:13]1[N:12]=[CH:11][C:10]([CH2:9][O:8][C:6]2[CH:5]=[CH:4][NH:3][C:2](=[O:19])[CH:7]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 580923082-Chloro-4-((6-methylpyridin-3-yl)methoxy)pyridine

Product 1

HCID 580922354-((6-Methylpyridin-3-yl)methoxy)pyridin-2(1H)-oneYield 77.5%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

2-Chloro-4-((6-methylpyridin-3-yl)methoxy)pyridine (4.20 g, 17.9 mmol) and ammonium acetate (6.91 g, 89.7 mmol) were heated at 110° C. in a mixture of formic acid (20 mL) and water (20 mL) for 5 days. The mixture was concentrated to remove most of the liquid and then adjusted to pH 8 with NaHCO3 solution. The solid was filtered off to provide the title compound (3.0 g, 77%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 11.27-11.04 (br s, 1H), 8.51 (s, 1H), 7.73 (d, J=7.1 Hz, 1H), 7.29-7.24 (m, 2H), 5.89 (d, J=7.2 Hz, 1H), 5.82 (s, 1H), 5.05 (s, 2H), 2.50 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove most of the liquid
  3. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-32ce5a6dd22a42a689d63bcb9e0bcece
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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