Phthalic Anhydride → 2-(3,3,3-Trifluoro-2-hydroxy-2-methylpropyl)-1H-isoindole-1,3(2H)-dione

HRID 887887Notes

Reaction equation

HRID 887887 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([OH:7])([CH3:6])[CH2:4][NH3+:5].[C:10]1(=O)[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[F:1][C:2]([F:9])([F:8])[C:3]([OH:7])([CH3:6])[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:11](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]1=[O:15]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 81531DiisopropylethylamineHCID 86657675HCID 86657675, compound

Product 1

HCID 673836442-(3,3,3-Trifluoro-2-hydroxy-2-methylpropyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture comprising 3,3,3-trifluoro-2-hydroxy-2-methyl-propyl-ammonium (0.9 g), phthalic anhydride (1.039 g) and DIPEA (2.188 ml) in chloroform (30 ml) was heated at 70° C. for 5 hours. After cooling to RT, the mixture was washed with water and passed through a phase separator. The organic phase was reduced to dryness. The crude product was purified by chromatography on silica, eluting in a 0% to 30% iso-hexane:EtOAc removed to give the title product; 1H NMR (400 MHz, Methanol-d4) δ 7.92 (2H, m), 7.85 (2H, m), 3.95 (2H, m), 1.36 (3H, s).

Workup

  1. washthe mixture was washed with water
  2. customThe crude product was purified by chromatography on silica
  3. washeluting in a 0% to 30% iso-hexane
  4. customEtOAc removed

Sources & evidence

ORD record
ord-246e82207b9d4c9fb802787ad100ca29
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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