Formic Acid → N-((4-bromopyridin-2-yl)methyl)formamide

HRID 2263537Notes

Reaction equation

HRID 2263537 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][NH2:9])[CH:3]=1.[CH:10](O)=[O:11]>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][NH:9][CH:10]=[O:11])[CH:3]=1

Participants

3

Procedure

20.00 g of C-(4-bromopyridin-2-yl)methylamine are taken up in 60 ml of formic acid and the solution is heated to reflux over 3 hours. The reaction solution is cooled to room temperature and concentrated by evaporation, and the residue is taken up in saturated aqueous sodium hydrogencarbonate solution (300 ml) and the aqueous solution extracted with dichloromethane (3×300 ml). The combined organic phases are washed with water (300 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60 F).

Workup

  1. temperaturethe solution is heated
  2. temperatureto reflux over 3 hours
  3. concentrationconcentrated by evaporation
  4. extractionthe aqueous solution extracted with dichloromethane (3×300 ml)
  5. washThe combined organic phases are washed with water (300 ml)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-bf1ecb4899cf41dfafd6b8ba40d4ceaa
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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