Ethylamine → 5-Bromo-2-ethyl-2,3-dihydro-1H-isoindol-1-one

HRID 1778733Notes

Reaction equation

HRID 1778733 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.[CH2:14]([NH2:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:16]([CH2:14][CH3:15])[CH2:12]2

Participants

6

Reactant 3

HCID 6341EthylamineHCID 11430Potassium CarbonateHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 231581465-Bromo-2-ethyl-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-bromo-2-(bromomethyl)benzoate (0.5 g, 2 mmol) (AstaTech Cat. No. 27012), ethylamine in THF (1.0 mL, 2.0 M) (Aldrich Cat. No. 395072), and potassium carbonate (0.34 g, 2.4 mmol) in ethanol (5 mL) in a sealed vial was stirred at 40° C. overnight. The solid was filtered off. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.28 g). LCMS (M+H)+=240.0/242.0.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-ad41058dab7e4ff88dc5becbbce6f0dc
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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