Water → 2-Chloro-5-nitro-N-{4-[(phenylmethyl)oxy]phenyl}-4-pyridineamine

https://huagongshe.com/reaction/1986379

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Triethylamine	HCID 8471	—
Reactant	4-Benzyloxyaniline hydrochloride	HCID 2723831	—
Reactant	2,4-Dichloro-5-nitropyridine	HCID 12275765	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-Chloro-5-nitro-N-{4-[(phenylmethyl)oxy]phenyl}-4-pyridineamine	HCID 86045153	92.1%

Reaction Conditions

Temperature	60 °C

Reaction Steps

The product of Example 1, Step 3 (15.2 g, 78.7 mmol), 4-benzyloxyaniline HCl (15.6 g, 78.7 mmol) and Et3N (27 mL, 196.9 mmol) were combined in DMF (125 mL) and heated to 60° C. for 1 h. The reaction mixture was cooled and H2O (200 mL) was added dropwise over 1 h. The resulting yellow/orange precipitate was filtered and washed with Et2O to provide the title compound as a yellow powder (25.8 g, 92%). MS (ES+) m/e 356 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07547779B2
Source dataset	uspto-grants-2009_06
ORD ID	ord-ee1afc2dcdc046a6a1b5abdfa073d197
Source note	uspto-grants-2009_06