Ethanol → HCID 22936243, compound

HRID 387804Notes

Reaction equation

HRID 387804 reaction equation
[C:1]([C:3]1[C:4]([NH2:19])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)#[CH:2].[Cl-].[NH4+].CN(C)C=O.C(O)C>[Fe].O>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:8]2[CH:7]=[CH:6][N:5]=[C:4]([NH2:19])[C:3]=2[C:1]#[CH:2])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22936488HCID 22936488, compound

Product 1

HCID 22936243HCID 22936243, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

3-(1-Ethynyl)-4-(4-nitrophenoxy)-2-pyridineamine (400 mg), iron powder (800 mg), ammonium chloride (1.6 g), dimethylformamide (3 ml), ethanol (1 ml) and water (1 ml) were stirred at 100° C. for 30 minutes. The mixture was filtered with celite, and then water and ethyl acetate were added to the filtrate 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 and the solvent was distilled off under reduced pressure to obtain 260 mg of the target substance as a brown solid.

Workup

  1. filtrationThe mixture was filtered with celite
  2. additionwater and ethyl acetate were added to the filtrate 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
  7. customto obtain 260 mg of the target substance as a brown solid

Sources & evidence

ORD record
ord-5722e70ca3964184b4c20b8c9818346e
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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