Phthalic Anhydride → 2-(1-hydroxy-2-methylpropan-2-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 872519Notes

Reaction equation

HRID 872519 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7]1(=O)[O:12][C:10](=[O:11])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12>>[OH:4][CH2:3][C:2]([N:1]1[C:10](=[O:11])[C:9]2[C:8](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]1=[O:12])([CH3:6])[CH3:5]

Participants

3

Reactant 2

HCID 6811Phthalic AnhydrideHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 8277892-(1-hydroxy-2-methylpropan-2-yl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 33%

Procedure

2-Amino-2-methyl-1-propanol (4.46 g, 50 mmol) and phthalic anhydride (7.41 g, 50 mmol) were heated at 170° C. for 30 minutes. Icewater was added to the cooled reaction mixture and then the mixture was extracted three times with DCM. Organic phase was dried over Na2SO4, filtered and evaporated to dryness. Crude product was purified by CombiFlash (column: silica, eluent: 0-10% MeOH in DCM) to obtain 3.611 g (33%) of the title compound. LC-MS: M+1=220.

Workup

  1. additionIcewater was added to the cooled reaction mixture
  2. extractionthe mixture was extracted three times with DCM
  3. dry with materialOrganic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customCrude product was purified by CombiFlash (column: silica, eluent: 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-efb87f9e720c4e02b222321f0d65bf58
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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