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2-Methyl-5-(2-methyl-4-nitrophenoxy)benzo[d]oxazole → 3-Methyl-4-(2-methylbenzo[d]oxazol-5-yloxy)benzenamine

HRID 240541
Notes
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Reaction equation

HRID 240541 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=3[CH3:21])=[CH:7][C:5]=2[N:6]=1.[H][H]>C(O)C.[Pd]>[CH3:21][C:13]1[CH:14]=[C:15]([NH2:18])[CH:16]=[CH:17][C:12]=1[O:11][C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 669369092-Methyl-5-(2-methyl-4-nitrophenoxy)benzo[d]oxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 669372733-Methyl-4-(2-methylbenzo[d]oxazol-5-yloxy)benzenamineYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-5-(2-methyl-4-nitrophenoxy)benzo[d]oxazole (671 mg, 2.36 mmol) in ethanol (10 mL) was added 10% palladium on carbon (50 mg, 0.047 mmol). The reaction mixture was subjected to 40 psi of hydrogen for 2.5 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was chromatographed to provide the product (0.411 g, 69%) as yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was chromatographed

Sources & evidence

ORD record
ord-ddbadea473d84e6d97d92ef8dd4792ee
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08648087B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes