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

HRID 49324Notes

Reaction equation

HRID 49324 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)(=O)C(Cl)=O.C(N(CC)CC)C.Cl.[CH3:25][NH:26][O:27][CH3:28]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([N:26]([O:27][CH3:28])[CH3:25])=[O:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 887075-Bromonicotinic acid

Product 1

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

40 g (198 mmol) of 5-bromonicotinic acid are dissolved in 300 mL of THF and treated with 19 mL of oxalyl chloride at 0° C. 66 mL (475 mmol) of triethylamine are then added, followed by 23.2 g (237 mmol) of N,O-dimethylhydroxylamine hydrochloride. After stirring at room temperature for 4 hours, the reaction medium is poured into water and extracted with ethyl acetate. The organic phase is separated out after settling, dried over magnesium sulphate and evaporated. 45.1 g (93%) of the expected product are collected in the form of a light brown oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is separated out
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. custom45.1 g (93%) of the expected product are collected in the form of a light brown oil

Sources & evidence

ORD record
ord-91cd43815bf04fe083f559c74e4d4a8d
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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