Ethanol → HCID 22936711, compound

HRID 387735Notes

Reaction equation

HRID 387735 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(O)C.CN(C)C=O>[Fe].O>[C:15]1([C:11]2[CH:10]=[C:9]([O:8][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:22][CH:21]=3)[CH:14]=[CH:13][N:12]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22936452HCID 22936452, compound

Product 1

HCID 22936711HCID 22936711, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

4-(4-nitrophenoxy)-2-phenylpyridine (490 mg), iron powder (1 g), ammonium chloride (2 g), ethanol (10 ml), dimethylformamide (10 ml) and water (5 ml) were stirred at 100° C. for 10 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-(2-phenylpyridin-4-yl)oxyaniline (460 mg) as a brown 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-0fe7c998802142b7b67bfd82ec6fb349
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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