Acetic Acid → HCID 89691123, compound

HRID 2203044Notes

Reaction equation

HRID 2203044 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([CH:12]1[CH2:15][C:14](=[O:16])[CH2:13]1)=O.[CH3:17]C(O)=O>CC#N>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]=[C:10]([CH:12]3[CH2:15][C:14](=[O:16])[CH2:13]3)[N:1]([CH3:17])[C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 89690351HCID 89690351, compound

Product 1

HCID 89691123HCID 89691123, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-(2-amino-4-bromophenyl)-3-oxocyclobutanecarboxamide (2.7 g) in CH3CN (20 ml) was added AcOH (2 ml), and the mixture was heated under reflux for 3 h. The mixture was concentrated in vacuo, and poured into saturated NaHCO3 solution. The mixture was extracted with EtOAc, washed with water and brine successively, dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (hexane/EtOAc) to afford the title compound (2.0 g) as an off-white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe mixture was concentrated in vacuo
  4. additionpoured into saturated NaHCO3 solution
  5. extractionThe mixture was extracted with EtOAc
  6. washwashed with water and brine successively
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-b12cfee236ab42f1be52748c637ff271
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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