1-Hydroxybenzotriazole → Methyl 3-cyano-4-hydroxybenzoate

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	Methyl 4-hydroxy-3-iodobenzoate	HCID 11346465	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Methyl 3-cyano-4-hydroxybenzoate	HCID 11769089	295.8%

Reaction Steps

To a solution of 2 (1.49 g, 2.29 mmol), HBTU (1.3 g, 3.44 mmol), HOBt (530 mg, 3.44 mmol), and N,O-dimethylhydroxylamine HCl salt (340 mg, 3.44 mmol) in DMF (20 mL) was added DIEA (785 uL, 4.58 mmol). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated. The resulting residue was purified using silica gel (Hexanes/EtOAc=1:3) to give pure compound 3 (1.20 g, 78%) as an off-white, foamy solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07582668B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-7aee4e25ee0b431780a2c64e304a49c6
Source note	uspto-grants-2009_09