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

HRID 1483833Notes

Reaction equation

HRID 1483833 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12](OCC)=O.NC1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+].CC(=O)OCC>O>[OH:24][CH:21]1[CH2:22][CH2:23][CH:12]([N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 812934-Aminocyclohexanol

Product 1

HCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneYield 56.82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 1,3-dioxoisoindoline-2-carboxylate (1.67 g, 7.19 mmol) in water (16 mL) was added 4-aminocyclohexanol (1.31 g, 8.63 mmol), followed by K2CO3 (1.59 g, 11.5 mmol). The mixture was stirred at room temperature for 2 h. TLC (PE:EA=1:1) showed the reaction was complete. The mixture was filtered and the solid was dried under vacuum to give 2-(4-hydroxycyclohexyl)isoindoline-1,3-dione (1 g, 56.82%) as a brown solid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-043fd045f9b2434c90917f7136594493
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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