Ethanol → HCID 22936276, compound

HRID 387738Notes

Reaction equation

HRID 387738 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(O)C.CN(C)C=O>[Fe].O>[C:15]1([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22936250HCID 22936250, compound

Product 1

HCID 22936276HCID 22936276, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

4-(4-Nitrophenoxy)-3-phenylpyridine (150 mg), iron powder (300 mg), ammonium chloride (600 mg), ethanol (5 ml), dimethylformamide (5 ml) and water (2.5 ml) were stirred at 100° C. for 15 minutes. The mixture was filtered with celite, water was added to the filtrate, and extraction was performed with ethyl acetate. The organic layer was washed 5 times with water, and then the solvent was distilled off under reduced pressure to obtain 4-(3-phenylpyridin-4-yl)oxyaniline (84 mg) as a yellow oil.

Workup

  1. filtrationThe mixture was filtered with celite, water
  2. additionwas added to the filtrate, and extraction
  3. washThe organic layer was washed 5 times with water
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1c3b34571c1b4fa4aff5f9c99912b989
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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