Methylamine → 7-Methoxy-2-methylisoindolin-1-one

HRID 1528167Notes

Reaction equation

HRID 1528167 reaction equation
[CH3:1][NH2:2].Br[CH2:4][C:5]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:6]=1[C:7](OCC)=[O:8]>CO>[CH3:17][O:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:5]2[C:6]=1[C:7](=[O:8])[N:2]([CH3:1])[CH2:4]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 10038926Ethyl 2-bromomethyl-6-methoxybenzoate

Product 1

HCID 847178487-Methoxy-2-methylisoindolin-1-oneYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methylamine (2 M in methanol) at 0° C. was added dropwise to a solution of 14.82 g of ethyl 2-bromomethyl-6-methoxybenzoate in methanol and the reaction medium was stirred for 5 hours at 0° C. and left to stir at ambient temperature for 2 days. The solvent was evaporated off and 30 ml of a saturated sodium hydrogen carbonate solution were added to the residue. The product was extracted with ethyl acetate (3×50 ml). The organic phases were combined, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel. 4.52 g of 7-methoxy-2-methyl-2,3-dihydroisoindol-1-one were obtained. Yield=47%.

Workup

  1. waitleft
  2. stirringto stir at ambient temperature for 2 days
  3. customThe solvent was evaporated off
  4. addition30 ml of a saturated sodium hydrogen carbonate solution were added to the residue
  5. extractionThe product was extracted with ethyl acetate (3×50 ml)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a7218bf7a10148d0be98924dc1846cc7
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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