Methylamine → HCID 6496944, compound

HRID 2288939Notes

Reaction equation

HRID 2288939 reaction equation
[C:1]1([O:13][CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.CN>ClCCl>[C:1]1([O:13][CH2:14][CH2:15][NH2:16])[CH:2]=[CH:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 2221790HCID 2221790, compound

Product 1

HCID 6496944HCID 6496944, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-([biphen-4-yloxy]ethyl)isoindoline-1,3-dione (1.5 g, 4.4 mmol) in dichloromethane (30 ml) was added methylarnine (33% solution in ethanol, 50 ml) and the solution was heated to reflux under an atmosphere of nitrogen for 2 hours. The mixture was cooled to ambient temperature, and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonium solution 95:5:0 to 94:5:1 as eluent) to give the title compound as a colourless solid (505 mg).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux under an atmosphere of nitrogen for 2 hours
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonium solution 95:5:0 to 94:5:1 as eluent)

Sources & evidence

ORD record
ord-c2b0d5e09afe4cd78a863b0cdfe207fb
Source dataset
uspto-grants-2000_07
Patent number
US06090852

Reaction notes

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