Ammonia → 5-bromo-2,3-dihydro-1H-isoindol-1-one

HRID 605946Notes

Reaction equation

HRID 605946 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1[CH2:11]Br.[NH3:14]>>[Br:10][C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[C:3](=[O:2])[NH:14][CH2:11]2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-oneYield 65%

Procedure

4-Bromo-2-bromomethyl-benzoic acid methyl ester (0.5 g, 16.2 mmol) is treated with methanolic ammonia (10 mL, 7 N NH3 in MeOH) for 5 minutes at 90° C. After cooling to room temperature a precipitate is formed, collected by filtration and washed with a small amount of methanol to afford the title compound as a colourless solid (224 mg, 65%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 4.41 (2H, s), 7.64 (1H, d), 7.70 (1H, d), 7.87 (1H, s), 8.67 (1H, br s). LCMS: Rt 2.49 min, (99.6%), m/z (APCI) 212 (M+H)+.

Workup

  1. customis formed
  2. filtrationcollected by filtration
  3. washwashed with a small amount of methanol

Sources & evidence

ORD record
ord-9dbf85091ef84fdf86dc1414a9e10ce0
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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