Diphenylamine → HCID 266861, compound

HRID 333555Notes

Reaction equation

HRID 333555 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[N+:21]([C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[N:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 11487DiphenylamineHCID 125741-Iodo-3-nitrobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 266861HCID 266861, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A 1 L round bottom flask was charged with diphenylamine (13.29 g, 79.0 mmol), 1-iodo-3-nitrobenzene (19.56 g, 79.0 mmol), palladium (II) acetate (0.70 g, 3.12 mmol), biphenyl-2-dicyclohexylphosphine (2.19 g, 6.25 mmol), sodium tert-butoxide (10.48 g, 109 mmol) and toluene (400 mL). This was stirred at reflux for 18 h. The mixture was then filtered. The filtrate was concentrated in vacuo, and the crude product was chromatographed (silica gel) using a gradient of 10-20% dichloromethane in hexane to give 3-nitro-N,N-diphenylaniline (14.15 g, 62%) as an orange solid.

Workup

  1. temperatureat reflux for 18 h
  2. filtrationThe mixture was then filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe crude product was chromatographed (silica gel)

Sources & evidence

ORD record
ord-e33ac8d3f69b4292a2b02b377397c317
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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