1-Chloro-2-nitrobenzene → N-(4-Methoxyphenyl)-2-nitroaniline

Participants

Role	Name	HCID	Charge
Reactant	1-Chloro-2-nitrobenzene	HCID 6945	—
Reactant	P-Anisidine	HCID 7732	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Catalyst	Sodium t-butoxide	HCID 23676156	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Dodecane	HCID 8182	—
Product	N-(4-Methoxyphenyl)-2-nitroaniline	HCID 618504	96%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Pd(dba)2 (5.8 mg, 0.01 mmol, 1 mol % Pd), ligand 2 (see FIG. 1) (4.2 mg, 0.01 mmol) and NaOt-Bu (1 mg, 0.01 mmol) were stirred in 1 mL DME (anhy). After 10 minutes, the solution was added to a test tube containing (under an Argon atmosphere) K3PO4 (297 mg, 1.4 mmol), 2-nitrochlorobenzene (158 mg, 1.0 mmol), and p-anisidine (148 mg, 1.2 mmol). The test tube was capped and heated at 100° C. for 35 hours. The reaction mixture was cooled to r.t., diluted with ether and dodecane was added as an internal standard. The reaction mixture was purified by column chromatography (10% EtOAc/hexanes) to yield 234 mg (96% yield) of the product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06888029B2
Source dataset	uspto-grants-2005_05
ORD ID	ord-14a8a2cd95024fb89dbc876be5d2f13f
Source note	uspto-grants-2005_05