Acetonitrile → HCID 69430046, compound

HRID 1269908Notes

Reaction equation

HRID 1269908 reaction equation
C(#N)C.C(=O)([O-])[O-].[K+].[K+].[C:10]([N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])(OCC)=O.Cl.N[C@@H:28]1[C:33](C)([CH3:34])[CH2:32][CH2:31][C@H:30]([OH:36])[CH2:29]1>O>[OH:36][C@@H:30]1[CH2:31][C@H:10]([N:15]2[C:16](=[O:25])[C:17]3[C:18](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:20])[C:33]([CH3:34])([CH3:32])[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 69431379HCID 69431379, compound

Product 1

HCID 69430046HCID 69430046, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetonitrile (5 ml), potassium carbonate (3.1 mmol, 423 mg) and N-carboethoxyphthalimide (3.1 mmol, 670 mg) were added to a solution of cis-3-amino-4,4-dimethylcyclohexanol hydrochloride (500 mg, 2.8 mmol) in water (10 ml), and the resulting mixture was stirred as it was for 2 hours. The crystals precipitated were collected by filtration and then recrystallized from chloroform-diethyl ether to obtain cis-2-(5-hydroxy-2,2-dimethylcyclohexyl)-1H-isoindole-1,3(2H)-dione (400 mg, 53%, containing about 10% of trans isomer) as white powder.

Workup

  1. customThe crystals precipitated
  2. filtrationwere collected by filtration
  3. customrecrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-3ffc1d20cc4c4fcdb36191bd40a44a50
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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