Water → 1-benzyl-5-bromo-3-nitro-1H-pyridin-2-one

HRID 2054586Notes

Reaction equation

HRID 2054586 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([N:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]1=[O:8])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178418997HCID 178418997, compound

Product 1

HCID 596559621-benzyl-5-bromo-3-nitro-1H-pyridin-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-bromo-3-nitro-pyridin-2-ol (5.0 g, 22.8 mmol) and K2CO3 (9.5 g, 3 equiv., 69 mmol) in DMF (25 mL) was treated with benzyl bromide (4.3 g, 1.1 equiv., 25 mmol) and heated to 50° C. After stirring overnight, the solution was poured into water (150 mL) and extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (30-40% ethyl acetate in heptane) afforded 1-benzyl-5-bromo-3-nitro-1H-pyridin-2-one as a yellow solid (5.56 g, 79%).

Workup

  1. extractionextracted with ethyl acetate (2×150 mL)
  2. washThe combined organic layers were washed with sat'd aq NaCl
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (30-40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-7c02df3570a842edb59b7f10f98b402d
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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