N-Methylaniline → 2-Methyl-4-(N-methyl phenylamino)indene

HRID 222484Notes

Reaction equation

HRID 222484 reaction equation
CC([O-])(C)C.[Na+].[CH3:7][C:8]1[CH2:9][C:10]2[C:15]([CH:16]=1)=[C:14](Cl)[CH:13]=[CH:12][CH:11]=2.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.O>[CH3:7][C:8]1[CH2:9][C:10]2[C:15]([CH:16]=1)=[C:14]([N:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18])[CH:13]=[CH:12][CH:11]=2

Participants

7

Reactant 3

HCID 7515N-MethylanilineHCID 120107424-Chloro-2-methyl-1H-indeneHCID 23676156Sodium t-butoxide

Product 1

HCID 596151212-Methyl-4-(N-methyl phenylamino)indeneYield 69.4%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Pd(dba)2 (0.25 g, 0.4 mmol, 1.4 mol %), PtBu3 (0.11 g, 0.5 mmol, 1.8 mol %), NaOtBu (4.5 g, 45.4 mmol, 1.5 eq), 2-methyl-4-chloroindene (5 g, 30 mmol, 1 eq) and N-methyl phenylamine (3.25 g, 30 mmol, 1 eq.) were mixed together and stirred at 70° C. After 2 h of stirring, the reaction was cooled down and H2O was added. The formed layers were separated and the organic phase was washed with NH4C1 and H2O. The organic layer was then dried over MgSO4, filtered and concentrated. Chromatography over SiO2 (Hexan/CH2Cl2:2/1) gave a green oil (4.9 g) in 68% yield.

Workup

  1. stirringAfter 2 h of stirring
  2. temperaturethe reaction was cooled down
  3. customThe formed layers were separated
  4. washthe organic phase was washed with NH4C1 and H2O
  5. dry with materialThe organic layer was then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e19a1d78ddd46978ebc8bb09b8b6df5
Source dataset
uspto-grants-2012_06
Patent number
US08207281B2

Reaction notes

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