Sodium Carbonate → 2-Ethoxycarbonyl-4-nitroisoindoline

HRID 1494840Notes

Reaction equation

HRID 1494840 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:17]([O-:19])=[O:18])[CH2:9]1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(Cl)(Cl)Cl>[CH2:30]([O:29][C:27]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:17]([O-:19])=[O:18])[CH2:9]1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 147958602-Benzyl-4-nitroisoindoline

Product 1

HCID 198284912-Ethoxycarbonyl-4-nitroisoindolineYield 73.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.54 g of 2-benzyl-4-nitroisoindoline was dissolved in 10 ml of chloroform, and 1.27 g of sodium carbonate was added to the solution. To the mixture was added dropwise 1.30 g of ethyl chloroformate under ice-cooling while stirring. After the addition, the stirring was continued for 20 hours at room temperature. The insoluble materials were removed by filtration and the filtrate was washed with water, 5% hydrochloric acid, and then with water. The mixture was concentrated and recrystallized from a chloroform-ether mixed solvent to obtain 1.73 g of 2-ethoxycarbonyl-4-nitroisoindoline.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. customThe insoluble materials were removed by filtration
  4. washthe filtrate was washed with water, 5% hydrochloric acid
  5. concentrationThe mixture was concentrated
  6. customrecrystallized from a chloroform-ether mixed solvent

Sources & evidence

ORD record
ord-66a3af59fa604904a673c53fc15fa088
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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