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

HRID 252351Notes

Reaction equation

HRID 252351 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 is 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 60F).

Workup

  1. temperaturethe solution is heated
  2. temperatureto reflux over 3 hours
  3. concentrationconcentrated by evaporation
  4. extractionthe aqueous solution is 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-6fe4be815d1942bcaeb39e279730fdc3
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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