Ammonium Acetate → 4-(Pyridin-2-ylmethoxy)pyridin-2(1H)-one

HRID 469688Notes

Reaction equation

HRID 469688 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=1.C([O-])(=[O:18])C.[NH4+]>C(O)=O.O>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][O:8][C:6]1[CH:5]=[CH:4][NH:3][C:2](=[O:18])[CH:7]=1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 580922552-Chloro-4-(pyridin-2-ylmethoxy)pyridine

Product 1

HCID 579502834-(Pyridin-2-ylmethoxy)pyridin-2(1H)-oneYield 83%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

2-Chloro-4-(pyridin-2-ylmethoxy)pyridine (4.10 g, 18.5 mmol) and ammonium acetate (7.21 g, 92.3 mmol) were heated to 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 resulting solid was filtered off to provide the title compound (3.1 g, 83%) as a white solid: ESI MS m/z 203 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-bf1af0f2e9624a908f787933cb209bef
Source dataset
uspto-grants-2014_01
Patent number
US08629158B2

Reaction notes

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