Phthalic Anhydride → HCID 58215795, compound

HRID 593683Notes

Reaction equation

HRID 593683 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-3f8bd077d4724a40a6629a13c2b5ccbd
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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