Aniline → Diphenylamine

HRID 1871016Notes

Reaction equation

HRID 1871016 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.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]>[C:2]1([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 7964ChlorobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphine

Product 1

HCID 11487DiphenylamineYield 75%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

The above general procedure was followed using chlorobenzene (135 mg, 1.20 mmol) and aniline (93 mg, 1.00 mmol) with 5 mol % Pd(dba)2 and 4 mol % tri-t-butylphosphine in 2.0 mL of toluene. After 25 hours, the reaction mixture was adsorbed onto silica gel and chromatographed with 2.5% ethyl acetate/hexanes to give 126 mg (75%) of diphenylamine as an off-white solid.

Workup

  1. customchromatographed with 2.5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f0666da5cf2143c48e589ec75538d957
Source dataset
uspto-grants-2000_08
Patent number
US06100398

Reaction notes

Loading…