Methylamine → 5-Bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 2203217Notes

Reaction equation

HRID 2203217 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([CH2:12]Br)[CH:3]=1.[CH3:14][NH2:15]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:7])[N:15]([CH3:14])[CH2:12]2

Participants

3

Reactant 2

HCID 6329MethylamineHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 231581695-Bromo-2-methyl-2,3-dihydro-1H-isoindol-1-oneYield 99.7%

Conditions

Temperature
90 °C

Procedure

Methyl 4-bromo-2-(bromomethyl)benzoate (0.153 g, 0.497 mmol) was suspended in methanamine (2M solution in MeOH, 2.484 mL, 4.97 mmol) and the mixture was heated to reflux (90° C.) for 24 hours. The reaction mixture was cooled, concentrated in vacuo, and dried under high vacuum to give the title compound (0.112 g). 1H NMR (500 MHz, CDCl3) δ ppm 3.19 (s, 3 H), 4.36 (s, 2 H), 7.57-7.62 (m, 2 H), 7.70 (d, J=8.30 Hz, 1 H); ESI-MS m/z [M+H]+ 226.3.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-28464130f93243db912b07ca9a6650ca
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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