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

HRID 1717808Notes

Reaction equation

HRID 1717808 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].N1C=CC=CC=1.Cl.[CH3:18][O:19][NH:20][CH3:21].O>S(Cl)(Cl)=O.ClCCl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([N:20]([O:19][CH3:18])[CH3:21])=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 887075-Bromonicotinic acid

Product 1

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideYield 97.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Heat a solution of 5-bromo-nicotinic acid (50 g, 248 mmol) in thionyl chloride (200 mL) to reflux. After 4 hours, cool to ambient temperature and concentrate under reduced pressure to give a residue. Dissolve residue in dichloromethane (1.0 L). Add pyridine (58.7 g, 743 mmol) followed by O,N-dimethyl-hydroxylamine hydrochloride (26.6 g, 272 mmol) and stir. After 18 hours, add water (1.0 L) and extract with dichloromethane. Combine the organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield the title product as a clear oil (59.1 g, 97%):1H NMR (DMSO-d6) δ 3.29 (bs, 3H), 3.57 (bs, 3H), 8.24 (dd, 1H), 8.75 (d, 1H), 8.83 (d, 1H).

Workup

  1. temperatureto reflux
  2. concentrationconcentrate under reduced pressure
  3. customto give a residue
  4. waitAfter 18 hours
  5. extractionextract with dichloromethane
  6. dry with materialdry with sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-e4720173c4e84117926eb506f939949b
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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