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

Participants

Role	Name	HCID	Charge
Reactant	N-Methylaniline	HCID 7515	—
Reactant	4-Chloro-2-methyl-1H-indene	HCID 12010742	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Water	HCID 962	—
Product	2-Methyl-4-(N-methyl phenylamino)indene	HCID 59615121	69.4%

Reaction Conditions

Temperature	70 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08207281B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-1e19a1d78ddd46978ebc8bb09b8b6df5
Source note	uspto-grants-2012_06