Methylamine → 6-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 82048

Reaction equation

HRID 82048 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH2:11]Br.[CH3:14][NH2:15]>C1COCC1>[Br:10][C:8]1[CH:9]=[C:4]2[C:5]([CH2:11][N:15]([CH3:14])[C:3]2=[O:2])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate

Product 1

HCID 469420086-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-oneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 5-bromo-2-bromomethyl-benzoic acid methyl ester (1.00 g, 3.25 mmol) in THF (6.5 mL) was a solution of methylamine in THF (2M, 8.12 mL, 16.24 mmol). The reaction mixture was heated at 50° C. for 4 hours and then concentrated under vacuum. The residue was taken up in EtOAc and the organic layer was then washed with an aqueous 1M HCl solution, brine, dried (Na2SO4), filtered, concentrated under vacuum to give the title compound (0.73 g, 100%) as a yellow solid.

Workup

  1. concentrationconcentrated under vacuum
  2. washthe organic layer was then washed with an aqueous 1M HCl solution, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6e174c0561454a2d8fc1dd1e6727ca38
Source dataset
uspto-grants-2014_09
Patent number
US08846712B2

Linked notes

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