Potassium Carbonate → HCID 57309247, compound

HRID 1492459Notes

Reaction equation

HRID 1492459 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([C:13]([O:15][CH2:16][C:17]([Cl:20])([Cl:19])[Cl:18])=[O:14])[CH:9]=2)[CH:5]=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][CH2:16][C:17]([Cl:20])([Cl:18])[Cl:19])=[O:14])[CH2:7]2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57229321HCID 57229321, compound

Product 1

HCID 57309247HCID 57309247, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 5-nitroisoindol-2-carboxylic acid, 2,2,2-trichloroethyl ester (2.0 g, 5.9 mmol, title A compound) in ethyl acetate (20 mL) was treated with stannous chloride hydrate (6.6 g, 29.3 mmol) and the reaction mixture was heated under reflux for three hours. It was basified with saturated potassium carbonate solution, diluted with ethyl acetate (200 mL) and filtered through a celite pad. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine (100 mL), dried over anhydrous magnesium sulfate and evaporated in vacuo to give the title compound (1.6 g, 88.6%) as an oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for three hours
  3. filtrationfiltered through a celite pad
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine (100 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-80edeac36de74fcaad1d09ff1e80d76c
Source dataset
uspto-grants-1994_12
Patent number
US05374643

Reaction notes

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