2-[4-(4-Nitrophenoxy)phenyl]oxazole → 4-[4-(2-Oxazolyl)phenoxy]benzenamine

HRID 16486Notes

Reaction equation

HRID 16486 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[O:16][CH:17]=[CH:18][N:19]=3)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.CO.[Pd]>[O:16]1[CH:17]=[CH:18][N:19]=[C:15]1[C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[CH:20]=[CH:21][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 1

HCID 684907472-[4-(4-Nitrophenoxy)phenyl]oxazole

Product 1

HCID 684898744-[4-(2-Oxazolyl)phenoxy]benzenamineYield 103.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 2-[4-(4-nitrophenoxy)phenyl]oxazole (2.6 g, 9.2 mmol) in a mixture of ethyl acetate (20 mL) and methanol (100 mL) was placed under a nitrogen atmosphere before the addition of catalyst palladium (10% on C, 0.65 g). The reaction mixture was placed under a hydrogen atmosphere at atmospheric pressure. After 3 hours, the reaction mixture was filtered through a pad of Celite and washed with methanol. The filtrate was concentrated to give the 2.4 g of 4-[4-(2-oxazolyl)phenoxy]benzenamine.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fa4b8e44b0774854983521e35d628d48
Source dataset
uspto-grants-2010_06
Patent number
US07737145B2

Reaction notes

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