HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

2-Methoxyaniline → 2-(2-(2-Methoxyphenyl)aminoanilin-5-yl)benzoxazole

HRID 74198
Notes
Print preview

Reaction equation

HRID 74198 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.C(=O)([O-])O.[Na+].[CH3:25][O:26][C:27]1[C:28]([NH2:33])=[CH:29][CH:30]=[CH:31][CH:32]=1.[H][H]>C(O)C.[C].[Pd].O1CCCC1.O>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[NH2:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 70002-MethoxyanilineHCID 516892Sodium BicarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674989942-(2-(2-Methoxyphenyl)aminoanilin-5-yl)benzoxazoleYield 14%

Reagents, catalysts & solvents 4

HCID 178418390
HCID 178418390, compound
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added sodium hydrogen carbonate (195 mg, 2.32 mmol) and o-anisidine (357 mg, 2.90 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and this was extracted with chloroform. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The crystals obtained were added to a tetrahydrofuran (5 mL) solution containing 10% palladium-carbon (50 mg), a hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 8 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (51.9 mg, 14% yield) as red crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux
  3. extractionthis was extracted with chloroform
  4. customAfter the organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate, it
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customThe crystals obtained
  9. stirringthis was stirred at room temperature for 8 hours
  10. filtrationthis was filtered through Celite
  11. concentrationthe filtrate was concentrated
  12. customThe residue obtained
  13. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2268f5ec20db45e987b098a9c50318b5
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829035B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes