Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1622316Generated: November 1, 2026

Methanol → 5-[3-(N-hydroxyamidino)phenyl]-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione

https://huagongshe.com/reaction/1622316

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantTriethylamineHCID 8471—
ReactantHydroxyamine hydrochlorideHCID 443297—
Reactant5-(3-Cyanophenyl)-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dioneHCID 46863219—
SolventTetrahydrofuranHCID 8028—
Product5-[3-(N-hydroxyamidino)phenyl]-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dioneHCID 17851330891%

Reaction Steps

A solution of 5-(3-cyanophenyl)-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione (37 mg, 0.11 mmol), hydroxylamine hydrochloride (76 mg, 1.1 mmol) and triethylamine (0.16 mL, 1.1 mmol) in THF (0.65 mL)/methanol (1.3 mL) was heated under reflux for 2 hours. The solvent was removed under reduced pressure, and to the residue was added water (4 mL). The precipitated crystal was filtered and washed with water. The crystal was dried in vacuo at 50° C., to give the titled compound as a light gray crystal (36 mg, 91%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08778933B2
Source datasetuspto-grants-2014_07
ORD IDord-d36a10281a974126980d4beb268f8313
Source noteuspto-grants-2014_07