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

HRID 708600Notes

Reaction equation

HRID 708600 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 (2X10 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 (2X10 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-5810452b91d349bd9a74adcd2aeb8f0a
Source dataset
uspto-grants-2015_11
Patent number
US09175003B2

Reaction notes

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