N,O-Dimethylhydroxylamine → HCID 86647313, compound

HRID 1187031Notes

Reaction equation

HRID 1187031 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([C:14]([OH:16])=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[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([C:14]([N:31]([CH3:32])[O:30][CH3:29])=[O:16])[O:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 66644015HCID 66644015, compound

Product 1

HCID 86647313HCID 86647313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-bromo-7-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid (5.9 g, 21 mmol) and CDI (4.0 g, 25 mmol) in 60 mL of dry DCM was stirred at r.t. for 0.5 hours and then O,N-dimethyl-hydroxylamine (2.4 g, 25 mmol) was added. The result mixture was stirred overnight. The solvents were removed under vacuum, and the residue was purified by column to give 6-bromo-N-methyl-N,7-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 column

Sources & evidence

ORD record
ord-f10d6f748d454290a89dce5d2822d0d4
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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