Water → 5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide

HRID 82255Notes

Reaction equation

HRID 82255 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)([C:13](Cl)=[O:14])=O.C[CH2:18][N:19](CC)CC.O>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([N:19]([O:14][CH3:13])[CH3:18])=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 887075-Bromonicotinic acid

Product 1

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-nicotinic acid (100 g, 0.5 mol) in THF (2 L) at 0° C., (COCl)2 (95 g, 0.74 mol) was added. After stirring for 0.5 h, Et3N (152 g, 1.5 mol) and O, N-dimethyl hydroxylamine. HCl (140 g, 1.5 mol) were added. The reaction mixture was stirred at room temperature for 2.5 hours and then water (200 mL) and EtOAc (500 mL) were added. The organic layer was separated, dried (MgSO4) and concentrated in vacuo to afford 5—the title compound as a brown oil in 82% yield, 100%.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2.5 hours
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37dae837f84e4b7686f4ef84c442d4b9
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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