Ethanol → HCID 22936480, compound

HRID 387821Notes

Reaction equation

HRID 387821 reaction equation
[CH:1]1([C:5]([N:7]([C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)[CH:17]=[CH:16][N:15]=2)C(C2CCC2)=O)=[O:6])[CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+].CN(C)C=O.C(O)C>[Fe].O>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:18]2[CH:17]=[CH:16][N:15]=[C:14]([NH:7][C:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)=[O:6])[CH:19]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57933355HCID 57933355, compound

Product 1

HCID 22936480HCID 22936480, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

N1-Cyclobutanecarbonyl-N1-[4-(4-nitrophenoxy)-2-pyridyl]-1-cyclobutanecarboxamide (720 mg), iron powder (1.4 g), ammonium chloride (2.4 g), dimethylformamide (52 ml), ethanol (2 ml) and water (1 ml) were stirred at 100° C. for 15 minutes. The mixture was filtered with celite, and then water and ethyl acetate were added for extraction. The organic layer was washed 5 times with ammonium chloride water and then dried over magnesium sulfate. The drying agent was filtered off, the solvent was distilled off under reduced pressure, ethyl acetate and hexane were added to the residue and the precipitated solid was filtered out to obtain 130 mg of a solid.

Workup

  1. filtrationThe mixture was filtered with celite
  2. additionwater and ethyl acetate were added for extraction
  3. washThe organic layer was washed 5 times with ammonium chloride water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure, ethyl acetate and hexane
  7. additionwere added to the residue
  8. filtrationthe precipitated solid was filtered out

Sources & evidence

ORD record
ord-a1990f964ca14835871ad796d3825c0e
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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