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

HRID 1474278Notes

Reaction equation

HRID 1474278 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]([OH:14])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:27][O:28][NH:29][CH3:30]>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]([N:29]([CH3:30])[O:28][CH3:27])=[O:14]

Participants

5

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 666464675-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid

Product 1

HCID 866473105-bromo-N-methyl-N-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid (9.10 g, 35.4 mmol) and CDI (4.14 g, 42.5 mmol) in 200 mL of dry DCM was stirred at r.t. for 30 min and then O,N-dimethyl-hydroxylamine (5.99 g, 42.5 mmol) was added. The resulting mixture was stirred overnight. The solvents were removed under vacuum, and the residue was purified with silica gel column chromatography to give 5-bromo-N-methyl-N-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide. 1H-NMR (400 MHz, CDCl3) δ 7.40 (d, J=8.0 Hz, 1H), 6.99 (t, J=8.0 Hz, 1H), 6.93 (d, J=8.0 Hz, 1H), 5.63 (s, 1H), 4.23˜4.28 (m, 1H), 3.87˜3.92 (m, 1H), 3.71 (s, 3H), 3.19 (s, 3H), 2.71˜2.87 (m, 2H).

Workup

  1. stirringThe resulting mixture was stirred overnight
  2. customThe solvents were removed under vacuum
  3. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-9340a06822f74b2f859d5d963795274b
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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