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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 389929Generated: October 30, 2026

Ammonium Chloride → 5-[2,4-bis(benzyloxy)-5-chlorophenyl]-4-amino-N-ethylisoxazole-3-carboxamide

https://huagongshe.com/reaction/389929

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmonium ChlorideHCID 25517—
Reactant5-[2,4-bis(benzyloxy)-5-chlorophenyl]-N-ethyl-4-nitroisoxazole-3-carboxamideHCID 56926810—
CatalystZincHCID 23994—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product5-[2,4-bis(benzyloxy)-5-chlorophenyl]-4-amino-N-ethylisoxazole-3-carboxamideHCID 5692681187.1%

Reaction Conditions

Temperature0 °C

Reaction Steps

A solution of 5-(2,4-bis-benzyloxy-5-chloro-phenyl)-4-nitro-isoxazole-3-carboxylic acid ethylamide (1 g, 1.97 mmol) in THF (7 ml) was added to a solution of NH4Cl (2.7 g, 50 mmol) in water (15 ml). Zinc dust (4 g, 61 mmol) was then added portion wise over 15 min with stirring at 0° C. After 30 min at 0° C., the mixture was filtered and the resulting cake was rinsed with MeOH. The combined filtrate were evaporated under vacuo to give 5-[2,4-bis(benzyloxy)-5-chlorophenyl]-4-amino-N-ethylisoxazole-3-carboxamide (820 mg, 82%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08383616B2
Source datasetuspto-grants-2013_02
ORD IDord-7aaa0072f0224065aa573549da319d11
Source noteuspto-grants-2013_02