Diphenylamine → 2'-Nitro-N,N-diphenyl[1,1'-biphenyl]-4-amine

HRID 1914406Notes

Reaction equation

HRID 1914406 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.[C:17]1([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[Na])(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=C(C)C=1>[C:24]1([N:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 11487DiphenylamineHCID 2355494'-Chloro-2-nitro-1,1'-biphenylHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 689273222'-Nitro-N,N-diphenyl[1,1'-biphenyl]-4-amineYield 47.8%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 7929M-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

A mixed solution of 2.0 g of 2-(4-chlorophenyl)nitrobenzene, 1.7 g of diphenylamine, 0.99 g of t-butoxysodium, 0.19 g of (tris-t-butylphosphine)tetrafluoroborate, 0.43 g of bis(dibenzylideneacetone)palladium(0) and 30 ml of m-xylene was heated and stirred under a nitrogen gas stream at 140° C. for 5 hours. The solution was cooled to room temperature and filtered through Celite. The filtrate was evaporated, and then the concentrate was purified by silica gel column chromatography and vacuum-dried to obtain 1.5 g of 2-(4-diphenylaminophenyl)nitrobenzene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customThe filtrate was evaporated
  4. customthe concentrate was purified by silica gel column chromatography
  5. customvacuum-dried

Sources & evidence

ORD record
ord-44867f82eb1343d68e720ccc6377a44a
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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