Hydrochloric Acid → 1-benzyl-4-(benzyloxy)-6-methylpyridin-2(1H)-one

HRID 1831883Notes

Reaction equation

HRID 1831883 reaction equation
[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:10][C:9]1=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 546786591-benzyl-4-hydroxy-6-methylpyridin-2(1H)-one

Product 1

HCID 101495921-benzyl-4-(benzyloxy)-6-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

1-benzyl-4-hydroxy-6-methylpyridin-2(1H)-one (10 mmol, 2.15 g), dichloromethane (100 mL), benzylbromide (11 mmol, 1.88 g), sodium hydroxide (2.5 N, 20 mmol, 8 mL), and benzyltriethylammonium chloride (0.5 g) were vigorously stirred at room temperature for 16 h. Hydrochloric acid (1 N) was added until the mixture produced an acidic reaction to pH paper. The mixture was then extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The product was obtained by flash chromatography eluting with ethyl acetate:hexanes (1:2). The appropriate fractions were concentrated to a clear oil. (1.3 g, 43%): 1H NMR (DMSO-d6/300 MHz) δ: 7.4-7.1 (m, 10H), 6.0-5.9 (m, 2H), 5.2 (s, 2H), 5.1 (s, 2H), 2.2 (s, 3H). ES HRMS m/z 306.147 (M+H, C20H19NO2 requires 306.149).

Workup

  1. customproduced
  2. customan acidic reaction
  3. extractionThe mixture was then extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was obtained by flash chromatography
  9. washeluting with ethyl acetate:hexanes (1:2)
  10. concentrationThe appropriate fractions were concentrated to a clear oil

Sources & evidence

ORD record
ord-8ab11c0724084fbeb547eff5c19b46a6
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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