Hydrochloric Acid → 1-benzyl-4-[(3-chlorobenzyl)oxy]-6-methylpyridin-2(1H)-one

HRID 1831886Notes

Reaction equation

HRID 1831886 reaction equation
BrC1C=CC(S([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14](=[O:26])[CH:13]=2)(=O)=O)=CC=1.[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]O.[OH-].[Na+].Cl>CN(C=O)C>[CH2:19]([N:15]1[C:16]([CH3:18])=[CH:17][C:12]([O:11][CH2:31][C:30]2[CH:33]=[CH:34][CH:35]=[C:28]([Cl:27])[CH:29]=2)=[CH:13][C:14]1=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 701173-Chlorobenzyl alcoholHCID 865915871-Benzyl-6-methyl-2-oxo-1,2-dihydropyridin-4-yl 4-bromobenzenesulfonate

Product 1

HCID 101934871-benzyl-4-[(3-chlorobenzyl)oxy]-6-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-benzyl-6-methyl-2-oxo-1,2-dihydropyridin-4-yl 4-bromobenzenesulfonate (3.0 mmol, 1.3 g), N,N′-dimethylformamide (30 mL), 3-chlorobenzyl alcohol (3.0 mmol, 0.43 g), and sodium hydroxide (60%, 3.3 mmol, 0.13 g) were stirred at room temperature under nitrogen for 4 hours. Hydrochloric acid (1 N, 10 mL) was added and the mixture extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and brine. After drying over magnesium sulfate and concentrating, the mixture was purified by flash column chromatography eluting with ethyl acetate:hexanes (1:1) to obtain a light yellow oil. (14.3 g, 64%): 1H NMR (DMSO-d6/300 MHz) δ: 7.4-7.0 (m, 10H), 6.0-5.8 (m, 2H), 5.2 (s, 2H), 5.0 (s, 2H), 2.1 (s, 3H). ES HRMS m/z 340.110 (M+H, C20H18NO2Cl requires 340.110).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×25 mL)
  2. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialAfter drying over magnesium sulfate
  4. concentrationconcentrating
  5. customthe mixture was purified by flash column chromatography
  6. washeluting with ethyl acetate:hexanes (1:1)
  7. customto obtain a light yellow oil

Sources & evidence

ORD record
ord-550dfd9c9c014010a0da8ecf8ecea77a
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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