Ethanol → 4-(4-Aminophenoxy)-2-butyrylaminopyridine

HRID 1433590Notes

Reaction equation

HRID 1433590 reaction equation
[C:1]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl-].[NH4+].C(O)C.CN(C)C=O>[Fe].O>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH:12]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 229366772-Butyroylamino-4-(4-nitrophenoxy)pyridine

Product 1

HCID 229364634-(4-Aminophenoxy)-2-butyrylaminopyridine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.6 g of 2-butyrylamino-4-(4-nitrophenoxy)pyridine, 1.2 g of iron powder, 2.8 g of ammonium chloride, 10 ml of ethanol, 10 ml of dimethylformamide and 5 ml of water was vigorously stirred at 100° C. for 10 minutes. The reaction was filtered with celite, the solvent was distilled off under reduced pressure, and then water was added to the filtrate and extraction was performed with ethyl acetate. The extract was dried over magnesium sulfate and the solvent distilled off under reduced pressure to obtain 0.6 g of the target substance as a light yellow solid.

Workup

  1. filtrationThe reaction was filtered with celite
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionwater was added to the filtrate and extraction
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationthe solvent distilled off under reduced pressure
  6. customto obtain 0.6 g of the target substance as a light yellow solid

Sources & evidence

ORD record
ord-545756bf615d40e0af7885968c46675f
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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