Hydrazine hydrate (1:1) → 4-(2,3-dimethylphenoxy)aniline

Participants

Role	Name	HCID	Charge
Reactant	Hydrazine hydrate (1:1)	HCID 24654	—
Reactant	1,2-Dimethyl-3-(4-nitrophenoxy)benzene	HCID 618129	—
Catalyst	Palladium	HCID 23938	—
Solvent	Ethanol	HCID 702	—
Product	4-(2,3-dimethylphenoxy)aniline	HCID 7139200	105%

Reaction Conditions

Temperature	90 °C

Reaction Steps

2,3-dimethylphenyl 4-nitrophenyl ether (Intermediate 73, 865 mg) was dissolved in ethanol (10 mL) to give a pale yellow solution. Hydrazine hydrate 50% (0.698 mL, 7.1 mmol) and Pd/C (37.8 mg, 0.36 mmol) were added. The reaction mixture was stirred at 90° C. for 1 hour. The reaction mixture was filtered and the organic phase was evaporated under vacuum to afford the title compound as a pale yellow oil (796 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09216967B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-a242059693db49dd9403348fc0f5d883
Source note	uspto-grants-2015_12