Toluene → N,2,5-trimethyl-N-phenylaniline

HRID 227845

Reaction equation

HRID 227845 reaction equation
CC([O-])(C)C.[Na+].C1(C)C=CC=CC=1.[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[CH3:30]>CCOCC.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:30][C:24]1[CH:25]=[CH:26][C:27]([CH3:29])=[CH:28][C:23]=1[N:15]([CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7515N-MethylanilineHCID 32883Chloro-p-xyleneHCID 23676156Sodium t-butoxide

Product 1

HCID 11042050N,2,5-trimethyl-N-phenylanilineYield 95%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

An oven-dried test tube was purged with argon and charged with Pd2(dba)3 (4.6 mg, 0.005 mmol, 1.0 mol % Pd), 2 [Example 1] (6.0 mg, 0.015 mmol, 1.5 mol %), and NaOt-Bu (135 mg, 1.40 mmol). The test tube was fitted with a septum, then toluene (2.0 mL), N-methylaniline (135 μL, 1.25 mmol), and 2-chloro-p-xylene (135 μL, 1.01 mmol) were added. The mixture was stirred at 80° C. for 13 h, then cooled to room temperature, diluted with ether (20 mL), filtered and concentrated. The crude material was purified by flash chromatography on silica gel to afford 202 mg (95%) of a colorless oil.

Workup

  1. customAn oven-dried test tube was purged with argon
  2. customThe test tube was fitted with a septum
  3. temperaturecooled to room temperature
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-903dbd7f86834deb842b14999b59d176
Source dataset
uspto-grants-2009_07
Patent number
US07560582B2

Linked notes

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