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

HRID 1818494Notes

Reaction equation

HRID 1818494 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 organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield the title compound 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. extractionextract with dichloromethane
  5. dry with materialCombine organic layers, dry with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-1c3ff63f69b247ad9c89c939c0248013
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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