Water → trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dione

HRID 2280786Notes

Reaction equation

HRID 2280786 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])O1.[CH2:12]1[CH:17]([NH2:18])[CH2:16][CH2:15][CH:14]([OH:19])[CH2:13]1.O>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:16]1[CH:17]([N:18]2[C:3](=[O:10])[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:11])[CH2:12][CH2:13][CH:14]([OH:19])[CH2:15]1

Participants

6

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 812934-Aminocyclohexanol

Product 1

HCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneYield 81%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of isobenzofuran-1,3-dione (90 g, 0.6 mol) and (1r,4r)-4-aminocyclohexanol (70 g, 0.6 mol) in toluene (250 mL) and DMF (250 mL) was stirred at 130° C. overnight. The reaction was cooled to room temperature, water was added and the product was filtered, washed with water and dried under vacuum to give the desired product as a white solid, which was used for the next step without further purification (119 g, 0.48 mol, yield: 81%). 1H NMR (400 MHz, CDCl3) δ ppm 7.84-7.79 (m, 2H), 7.72-7.68 (m, 2H), 4.18-4.10 (m, 1H), 3.80-3.73 (m, 1H), 2.40-2.29 (qd, J1=3.4 Hz, J2=130 Hz, 2H), 2.12-2.09 (dd, J=6.2 Hz, 2H), 1.78-1.74 (dd, J=6.6 Hz, 2H), 1.49-1.39 (qd, J1=3.3 Hz, J2=125 Hz, 2H).

Workup

  1. filtrationthe product was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d6241d4527b64239a1b43430b7f0eb4c
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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