Phthalic Anhydride → HCID 58215795, compound

HRID 1630953Notes

Reaction equation

HRID 1630953 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:9]1(=O)[O:14][C:12](=[O:13])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12>C(O)(=O)C>[Br:8][C:6]1[CH:7]=[C:2]([N:1]2[C:12](=[O:13])[C:11]3[C:10](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]2=[O:14])[CH:3]=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 58215795HCID 58215795, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A flask is charged with 3-amino-5-bromo pyridine (1.00 g, 5.78 mmol), phthalic anhydride (0.856 g, 5.78 mmol) and acetic acid (20 mL). The reaction is refluxed overnight. The reaction is then cooled to room temperature and concentrated in vacuo. The crude is dissolved in ethyl acetate and washed with water once. The organic layer is dried over sodium sulfate and concentrated in vacuo to afford 2-(5-bromo-pyridin-3-yl)-isoindole-1,3-dione. MS (ESI) m/z 305.1 (M+H)+

Workup

  1. temperatureThe reaction is refluxed overnight
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude is dissolved in ethyl acetate
  4. washwashed with water once
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b8ec72f421ba46bbb431669948c2e2a2
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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