Water → N-Cyclobutylmethyl-N-(6-methyl-5-nitro-pyridin-2-yl)-acetamide

HRID 879709Notes

Reaction equation

HRID 879709 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH:23]1[CH2:26][CH2:25][CH2:24]1.O>CN(C=O)C>[CH:23]1([CH2:22][N:8]([C:6]2[CH:5]=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([CH3:1])[N:7]=2)[C:9](=[O:11])[CH3:10])[CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734658(Bromomethyl)cyclobutaneHCID 4072726N-(6-methyl-5-nitropyridin-2-yl)acetamide

Product 1

HCID 67249447N-Cyclobutylmethyl-N-(6-methyl-5-nitro-pyridin-2-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-(6-Methyl-5-nitro-pyridin-2-yl)-acetamide (0.5 g) was taken in 5 mL anhydrous DMF. 3 eq of K2CO3 and 3 eq of bromomethyl-cyclobutane were added and heated at 80° C. for 24 h. Water was added to the reaction and the mixture extracted with EtOAc (2×10 mL). The organic layer was washed with water and brine and dried over Na2SO4. Solvent was concentrated and the residue was purified over silica to give N-Cyclobutylmethyl-N-(6-methyl-5-nitro-pyridin-2-yl)-acetamide LCMS (m/z): 264.

Workup

  1. extractionthe mixture extracted with EtOAc (2×10 mL)
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationSolvent was concentrated
  5. customthe residue was purified over silica

Sources & evidence

ORD record
ord-3e6b77fb615e4744b1c4cd54281396ac
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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