Phthalic Anhydride → 2-(5-Methylpyridin-2-yl)isoindoline-1,3-dione

HRID 1505051Notes

Reaction equation

HRID 1505051 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][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.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12](=[O:13])[C:11]3[C:10](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]2=[O:14])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 153482-Amino-5-methylpyridineHCID 81531Diisopropylethylamine

Product 1

HCID 109665522-(5-Methylpyridin-2-yl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture containing 5-methylpyridin-2-amine (5.4 g, 50 mmol), phthalic anhydride (8.88 g, 60 mmol) and DIEA (19 ml, 110 mmol) in toluene (30 ml) is refluxed for 18 hours, and cooled. The solvent is removed by rotary evaporation. The crude product is purified by silica gel flash chromatography to afford 2-(5-methylpyridin-2-yl)isoindoline-1,3-dione as a dark brown oil. LC-MS m/z: 239.1 (M+1).

Workup

  1. temperatureis refluxed for 18 hours
  2. temperaturecooled
  3. customThe solvent is removed by rotary evaporation
  4. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c767b0a952f548239499271ca6a84499
Source dataset
uspto-grants-2015_12
Patent number
US09216964B2

Reaction notes

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