2-Methoxy-4-(2-(pyridin-2-yl)ethyl)pyridine → 4-(2-(Pyridin-2-yl)ethyl)pyridin-2(1H)-one

HRID 2387519Notes

Reaction equation

HRID 2387519 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:5][N:4]=1>Cl>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][C:7]1[CH:6]=[CH:5][NH:4][C:3](=[O:2])[CH:8]=1

Participants

3

Reactant 1

HCID 592934092-Methoxy-4-(2-(pyridin-2-yl)ethyl)pyridine

Product 1

HCID 592934144-(2-(Pyridin-2-yl)ethyl)pyridin-2(1H)-oneYield 96.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Methoxy-4-(2-(pyridin-2-yl)ethyl)pyridine (200 mg, 0.93 mmol) was stirred in concentrated hydrochloric acid (5 mL) at 120° C. for 18 h and then concentrated. The residue was dissolved in MeOH (5 mL) and passed down an Isolute SCX-2 column (10 g). Elution with 7 N NH3 in MeOH and concentration of the eluent provided the title compound (180 mg, 96%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 8.45 (d, J=4.7 Hz, 1H), 7.75-7.71 (dd, J=7.8, 1.8 Hz, 1H), 7.32 (d, J=6.9 Hz, 1H), 7.28 (d, J=7.8 Hz, 1H), 7.27-7.23 (dd, J=7.8, 5.1 Hz, 1H), 6.34-6.29 (m, 2H), 3.08 (t, J=7.3 Hz, 2H), 2.92 (t, J=7.9 Hz, 2H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in MeOH (5 mL)
  3. washElution with 7 N NH3 in MeOH and concentration of the eluent

Sources & evidence

ORD record
ord-a68cb6d56bba4ea88e49d543ac7b4cff
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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