Ammonia → 2-Methyl-3-(4-pyridyl)propionamide

HRID 1896259Notes

Reaction equation

HRID 1896259 reaction equation
C(Cl)(=O)C(Cl)=O.[N:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH3:18])[C:15](O)=[O:16])=[CH:9][CH:8]=1.[NH3:19]>C(Cl)Cl>[N:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH3:18])[C:15]([NH2:19])=[O:16])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 121366342-Methyl-3-(pyridin-4-YL)propanoic acid

Product 1

HCID 121366362-Methyl-3-(4-pyridyl)propionamideYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (154 mg, 1.21 mmol) was added to a stirred solution of 2-((pyridin-4-yl)methyl)propanoic acid (100 mg, 0.61 mmol) in DCM (5 ml) at 0° C. under an atmosphere of nitrogen and stirred for 1.5 h at room temperature. The reaction mixture was concentrated under reduced pressure to give the crude acid chloride. Aqueous ammonia (5 ml) was added to the above acid chloride solution at 0° C. and stirred for 30 min. The reaction mixture was extracted with ethyl acetate. The combined ethyl acetate layer was washed with water followed by brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford 92.0 mg (92.9%) of 2-((pyridin-4-yl)methyl)propanamide as a pale brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give the crude acid chloride
  3. stirringstirred for 30 min
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washThe combined ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-20f7ec99b93d40eeb23a14b774cdf3d7
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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