Benzyl Chloride → 1,3-Dibenzyl-5-bromo-1H-pyridin-4-one

HRID 1364376Notes

Reaction equation

HRID 1364376 reaction equation
[CH2:1]([CH:8]1[C:13](=[O:14])[C:12]([Br:15])=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[O-].[Na+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[CH2:20]([N:10]1[CH:11]=[C:12]([Br:15])[C:13](=[O:14])[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 2723922Sodium ethoxideHCID 669366583-Benzyl-5-bromopyridin-4-one

Product 1

HCID 592740971,3-Dibenzyl-5-bromo-1H-pyridin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-benzyl-5-bromopyridin-4-one 12 (0.57 g, 2.16 mmol) and NaOEt (0.89 mL, 2.37 mmol) in absolute ethanol (20 mL) was refluxed with benzyl chloride (0.30 mL, 2.59 mmol) for 1 h under nitrogen. The solvent was distilled off to give a yellow residue which was purified by flash column chromatography on silica gel (dichloromethane:methanol, 98:2). Yield 1.31 g (96.7%), yellow solid, mp 120-121° C. 1H NMR (CDCl3, 500 MHz): δ 7.67 (d, 1H, J=2.4), 7.32-7.07 (m, 10H), 4.83 (s, 1H), 3.78 (s, 2H). 13C NMR (CDCl3, 125 MHz): δ 172.2, 139.6, 139.1, 137.6, 134.7, 129.9, 129.9, 129.3, 129.3, 129.2, 129.0, 128.6, 128.6, 127.5, 127.6, 126.4, 114.1, 60.3, 34.4. HRMS (M+H)+ calcd for C19H16BrNO 354.0494, found 354.0499.

Workup

  1. distillationThe solvent was distilled off
  2. customto give a yellow residue which
  3. customwas purified by flash column chromatography on silica gel (dichloromethane:methanol, 98:2)

Sources & evidence

ORD record
ord-6b8a5d5043c446b889d23f84812924da
Source dataset
uspto-grants-2011_02
Patent number
US07888375B2

Reaction notes

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