4-Isopropylaniline → N-(4-isopropylphenyl)-8-nitrochroman-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	4-Isopropylaniline	HCID 7464	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	8-nitro-3,4-dihydro-2H-1-benzopyran-4-carboxylic acid	HCID 17854141	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(4-isopropylphenyl)-8-nitrochroman-4-carboxamide	HCID 17854307	89.6%

Reaction Steps

To a solution of 8-nitrochroman-4-carboxylic acid (3.0 g) and 4-isopropylaniline (2.0 g) in dimethylformamide (30 mL) were added N-hydroxybenzotriazole hydrate (2.0 g) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (2.8 g), and the mixture was stirred at room temperature. After the completion of the reaction, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-(4-isopropylphenyl)-8-nitrochroman-4-carboxamide (4.1 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08198454B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-dfe9564918914edaac6cb49c840f9dfc
Source note	uspto-grants-2012_06