Sodium Hydroxide → N,2-dihydroxy-4-methoxybenzamide

An hydroxylamine solution was prepared by addition of aqueous sodium hydroxide (393 mg, 9.82 mmol)/water (1.6 ml) to a stirred solution of hydroxylamine hydrochloride (292 mg, 4.21 mmol) in water (3.5 ml). Immediately slowly added a solution of methyl 2-hydroxy-4-methoxybenzoate (511 mg, 2.81 mmol) in 1,4-dioxane (1.5 ml). The resulting reaction mixture was stirred at room temperature for 18 hours, under an argon atmosphere. The reaction mixture was concentrated on a rotary evaporator to half the original volume, and the product precipitated by addition of concentrated hydrochloric acid, keeping flask cool in an ice bath. Filtered the suspension to give 2-hydroxy-4-methoxybenzohydroxamic acid (476 mg, 92%) as a pale brown solid.

1. customThe resulting reaction mixture
2. concentrationThe reaction mixture was concentrated on a rotary evaporator to half the original volume
3. customthe product precipitated by addition of concentrated hydrochloric acid
4. temperaturecool in an ice bath
5. filtrationFiltered the suspension

ORD record

ord-afbcd2d599c64eb3bd6453ef3a4dddeb

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303026B2