Acetic Acid → HCID 89691123, compound

HRID 2202939Notes

Reaction equation

HRID 2202939 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:14][C:13](=[O:15])[CH2:12]2)=O)=[C:4]([NH:16][CH3:17])[CH:3]=1.CC(O)=O>CC#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:9]([CH:11]3[CH2:14][C:13](=[O:15])[CH2:12]3)[N:16]([CH3:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 89690206HCID 89690206, compound

Product 1

HCID 89691123HCID 89691123, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-(4-bromo-2-(methylamino)phenyl)-3-oxocyclobutanecarboxamide (2.7 g) in CH3CN (20 ml) was added glacial AcOH (2 ml) at room temperature, and then mixture was heated at reflux for 3 h. The mixture was then cooled to room temperature, concentrated in vacuo, and poured into ice-cold saturated NaHCO3 (100 ml). The mixture was extracted with EtOAc, and the extract was washed with water (100 ml) and brine (100 ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (2.0 g) as an off-white solid.

Workup

  1. temperaturemixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated in vacuo
  4. additionpoured into ice-cold saturated NaHCO3 (100 ml)
  5. extractionThe mixture was extracted with EtOAc
  6. washthe extract was washed with water (100 ml) and brine (100 ml)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-a609134eda2343958aa0b317f90438d1
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…