Ammonium Acetate → HCID 66618923, compound

HRID 406322Notes

Reaction equation

HRID 406322 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[C:5]([N:8]([CH2:11][C:12](=O)[CH3:13])[CH:9]=O)=[N:6][CH:7]=1.C([O-])(=O)C.[NH4+:21]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[C:5]([N:8]2[CH:11]=[C:12]([CH3:13])[N:21]=[CH:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 86662649HCID 86662649, compound

Product 1

HCID 66618923HCID 66618923, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of the crude N-(5-bromo-3-methoxypyridin-2-yl)-N-(2-oxopropyl)formamide (26.4 g), acetic acid (52.8 mL) and ammonium acetate (35.5 g) was stirred at 130° C. for one hour. The reaction solution was left to cool to room temperature and concentrated under reduced pressure. The residue diluted with ice water, ethyl acetate and aqueous ammonia, and the organic layer was separated. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate system) to obtain 5.69 g of the title compound. The property values of the compound are as follows.

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue diluted with ice water, ethyl acetate and aqueous ammonia
  5. customthe organic layer was separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-11be32469c0c4334b9b620c3b1e688d4
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

Loading…