Water → 110768-27-9

HRID 1515056Notes

Reaction equation

HRID 1515056 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[O:10]=[C:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=2)[C:13](=O)[O:12]1.O>CN(C=O)C>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[N:4]1[C:13](=[O:12])[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH:15]=2)[C:11]1=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 68962,6-DimethylanilineHCID 11089Trimellitic anhydride

Product 1

HCID 477697110768-27-9

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dimethylaniline (1.21 g) in DMF (15 mL) was added 1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic acid (1.92 g) and the mixture was stirred at room temperature for 18 h. The mixture was poured into water and the resulting precipitate was filtered, washed with water and dried under reduced pressure. The solid was suspended in HOAc (25 mL) and the mixture was heated at 110° C. for 4 h. The resulting solution was cooled and the solvent was removed under reduced pressure to give 2-(2,6-dimethylphenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid as an off-white solid, mp=210-213° C.; MS (m/z) 294 (M−1).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under reduced pressure
  4. temperaturethe mixture was heated at 110° C. for 4 h
  5. temperatureThe resulting solution was cooled
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3a623a6812a041f8b4439cd1dd3b5c44
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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