Phthalic Anhydride → 2-(5-Bromo-6-methylpyridin-3-yl)isoindoline-1,3-dione

HRID 2170358Notes

Reaction equation

HRID 2170358 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[Br:12][C:13]1[CH:14]=[C:15]([NH2:20])[CH:16]=[N:17][C:18]=1[CH3:19].C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:12][C:13]1[CH:14]=[C:15]([N:20]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH:16]=[N:17][C:18]=1[CH3:19]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 517045Sodium AcetateHCID 184588965-Bromo-6-methylpyridin-3-amine

Product 1

HCID 902813522-(5-Bromo-6-methylpyridin-3-yl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of phthalic anhydride (3.7 g, 25 mmol), 5-bromo-6-methylpyridin-3-amine (3.9 g, 20.85 mmol) and sodium acetate (1.5 g, 25 mmol) in glacial acetic acid (44 ml) was refluxed for overnight. After cooling down to room temperature, the precipitate was collected by vacuum filtration, washed with water, and dried to afford the title compound. MS (m/z) 318.91 [M+H]+.

Workup

  1. temperaturewas refluxed for overnight
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-9e633ec81837489f9151f650f16e40a6
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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