4-methoxy-N-(4-nitrophenyl)aniline → HCID 10243439, compound

HRID 1425579Notes

Reaction equation

HRID 1425579 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1>CC(O)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:17]=2[CH:18]=1)=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3

Participants

4

Reactant 1

HCID 27480234-methoxy-N-(4-nitrophenyl)aniline

Product 1

HCID 10243439HCID 10243439, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To 4-methoxy-N-(4-nitrophenyl)aniline (785 mg, 3.2 mmol) in 5 mL of AcOH was added Pd(OAc)2 (1.43 g, 6.4 mmol). The mixture was heated at 100° C. for 15 h under air atmosphere and cooled to rt and concentrated under reduced pressure. The residue was taken up in EtOAc (100 mL) and washed with NaHCO3 (2×100 mL) and water (100 mL). After solvent removal, the crude was purified with chromatography (hexane/EtOAc) to afford 3-methoxy-6-nitro-9H-carbazole as a orange solid (495 mg, 64%).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated under reduced pressure
  3. washwashed with NaHCO3 (2×100 mL) and water (100 mL)
  4. customAfter solvent removal
  5. customthe crude was purified with chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-f5757a4643744252ba87507373ee78db
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

Loading…