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

HRID 1187141Notes

Reaction equation

HRID 1187141 reaction equation
[Br:1][C:2]1[C:3]([O:15][CH3:16])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]([OH:14])=O)[O:7][CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:29][O:30][NH:31][CH3:32]>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:15][CH3:16])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]([N:31]([CH3:32])[O:30][CH3:29])=[O:14])[O:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 666463356-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid

Product 1

HCID 866473226-bromo-N-methyl-N,5-bis(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. stirringThe result mixture was stirred overnight
  2. customThe solvents were removed under vacuum
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-9f47e31ce6314793b30e8e0422da6465
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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