Phthalic Anhydride → HCID 67385713, compound

HRID 905957Notes

Reaction equation

HRID 905957 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH2:8][OH:9])[CH2:3]1.C(N(CC)CC)C.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12>C1(C)C=CC=CC=1>[OH:9][CH2:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@H:2]([N:1]2[C:20](=[O:21])[C:19]3[C:18](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17]2=[O:22])[CH2:3]1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 59401601HCID 59401601, compound

Product 1

HCID 67385713HCID 67385713, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Racemic trans 3-amino-cyclohexyl-methanol (0.65 g, 3.925 mmol) was taken up in toluene (25 mL) and triethylamine (1.6 mL, 11.5 mmol). Phthalic anhydride (0.581 g, 3.925 mmol) was added and the resulting mixture was stirred at reflux overnight. The reaction mixture was allowed to cool to RT before being washed with H2O. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and evaporated. The remaining solid was purified by SiO2 chromatography (40 g SiO2, hexanes/EtOAc 0 to 40%) to give 0.749 g of racemic trans-2-(3-hydroxymethyl-cyclohexyl)-isoindole-1,3-dione as a white solid (73% yield).

Workup

  1. temperatureat reflux overnight
  2. washbefore being washed with H2O
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe remaining solid was purified by SiO2 chromatography (40 g SiO2, hexanes/EtOAc 0 to 40%)

Sources & evidence

ORD record
ord-de3f51c84720471d80f1d183be8826dd
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

Loading…