Triethylamine → 4-methoxybenzoic acid N'-(4-amino-3-nitrobenzoyl)-hydrazide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	Benzoic acid, 4-amino-3-nitro-	HCID 74115	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	4-Methoxybenzohydrazide	HCID 76792	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-methoxybenzoic acid N'-(4-amino-3-nitrobenzoyl)-hydrazide	HCID 27169228	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of 4-amino-3-nitrobenzoic acid (3.64 g, 20 mmol) in DMF (50 mL) was added HOBT (2.70 g, 20 mmol) and EDCI (3.83 g, 20 mmol). After the addition, the solution was stirred at 25° C. for 10 min then 4-methoxybenzoic acid hydrazide (3.32 g, 20 mmol) was added and followed by the addition of NEt3 (8.35 mL, 60 mmol). The solution was stirred at 25° C. overnight and water was added. The resulting suspension was filtered and the solid was washed with water. The yellow solid was dried under reduced pressure and was purified by flash chromatography (heptane/EtOAc=1:3) to give the title compound. MS: m/z 331 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08217065B2
Source dataset	uspto-grants-2012_07
ORD ID	ord-341617adf6cc4325913d0a964ad1f9d9
Source note	uspto-grants-2012_07