Dimethylamine → 5-Bromo-N,N-dimethylpyridine-3-carboxamide

HRID 1820018Notes

Reaction equation

HRID 1820018 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH3:11][NH:12][CH3:13].C1COCC1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([N:12]([CH3:13])[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 27812235-Bromonicotinoyl chloride

Product 1

HCID 234370495-Bromo-N,N-dimethylpyridine-3-carboxamideYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a 100 mL round bottomed flask were added 5-bromonicotinoyl chloride (0.531 g, 2.41 mmol) and anhydrous pyridine (5 mL). A 2M solution of dimethylamine in THF (5 mL, 10.0 mmol) was added dropwise, and the reaction mixture was stirred at rt under N2 for 6 h after which it was concentrated under vacuum. The crude residue was partitioned between EtOAc and water. The layers were separated, and the organic phase was washed 3× with water, then treated with brine, dried (Na2SO4), filtered and concentrated to afford 5-Bromo-N,N-dimethyl-nicotinamide as a brown oil (0.4951 g, 89%). MS: m/z 229/231 [MH+].

Workup

  1. concentrationwas concentrated under vacuum
  2. customThe crude residue was partitioned between EtOAc and water
  3. customThe layers were separated
  4. washthe organic phase was washed 3× with water
  5. additiontreated with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4283b8a6fdce4292a7beaeabfba48b02
Source dataset
uspto-grants-2009_10
Patent number
US07601839B2

Reaction notes

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