4-Methoxybenzylamine → 2-(4-Methoxy-benzyl)-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile

HRID 2277632Notes

Reaction equation

HRID 2277632 reaction equation
CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=1[CH2:12]Br.[CH2:15]([NH2:24])[C:16]1[CH:23]=[CH:22][C:19]([O:20][CH3:21])=[CH:18][CH:17]=1>C1COCC1.CCOC(C)=O>[CH3:21][O:20][C:19]1[CH:22]=[CH:23][C:16]([CH2:15][N:24]2[CH2:12][C:5]3[C:4](=[CH:9][CH:8]=[C:7]([C:10]#[N:11])[CH:6]=3)[C:3]2=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 754524-MethoxybenzylamineHCID 23359115Methyl 2-(bromomethyl)-4-cyanobenzoate

Product 1

HCID 866859482-(4-Methoxy-benzyl)-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromomethyl-4-cyano-benzoic acid methyl ester (18.1 g, 71.24 mmol) in THF (300 mL) was added PMBNH2 (23.4 g, 178.1 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 16 hours. After vacuum filtration, the filtrate was concentrated in vacuo. The residue obtained was re-dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product which was purified by column chromatography (11.69 g, 56.0%) as a solid.

Workup

  1. filtrationAfter vacuum filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue obtained
  4. washwashed with water and brine
  5. customThe organic layer was dried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbdcaed28d3548e6b0dc1e0762227c3d
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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