Ethanol → HCID 22936243, compound

HRID 853326Notes

Reaction equation

HRID 853326 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-pyridinamine (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 aqueous ammonium chloride solution 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 aqueous ammonium chloride solution
  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-b60a1c5e63dc42fabc52a83363c00807
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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