5-(2-Methyl-4-nitrophenoxy)benzo[d]oxazole → 4-(Benzo[d]oxazol-5-yloxy)-3-methylbenzenamine

HRID 240577Notes

Reaction equation

HRID 240577 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][CH:11]=[N:10][C:9]=2[CH:13]=1>C(O)C.[Pd]>[O:12]1[C:8]2[CH:7]=[CH:6][C:5]([O:4][C:3]3[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:2]=3[CH3:1])=[CH:13][C:9]=2[N:10]=[CH:11]1

Participants

4

Reactant 1

HCID 669369305-(2-Methyl-4-nitrophenoxy)benzo[d]oxazole

Product 1

HCID 669372884-(Benzo[d]oxazol-5-yloxy)-3-methylbenzenamineYield 55.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-(2-methyl-4-nitrophenoxy)benzo[d]oxazole (1.65 g, 6.12 mmol) in ethanol was added Pd/C (0.130 g, 0.122 mmol). After stirring under hydrogen atmosphere for 16 hours, the mixture was filtered and the filtrate was concentrated to provide the product (0.81 g, 55%) as yellow oil.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c231314464c4c82a9eae3012e9cf287
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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