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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1187141Generated: November 1, 2026

N,O-Dimethylhydroxylamine → 6-bromo-N-methyl-N,5-bis(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide

https://huagongshe.com/reaction/1187141

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN,O-DimethylhydroxylamineHCID 14232—
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
Reactant6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acidHCID 66646335—
SolventDichloromethaneHCID 6344—
Product6-bromo-N-methyl-N,5-bis(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamideHCID 86647322—

Reaction Steps

A mixture of 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid (600 mg, 2.08 mmol) and CDI (475 mg, 2.93 mmol) in 20 mL of dry DCM was stirred at r.t. for 0.5 hours and then O,N-dimethyl-hydroxylamine (285 mg, 2.93 mmol) was added. The result mixture was stirred overnight. The solvents were removed under vacuum, and the residue was purified by preparative TLC to give 6-bromo-N-methyl-N,5-bis(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08673920B2
Source datasetuspto-grants-2014_03
ORD IDord-9f47e31ce6314793b30e8e0422da6465
Source noteuspto-grants-2014_03