Dimethylformamide → HCID 22827913, compound

HRID 622625Notes

Reaction equation

HRID 622625 reaction equation
CN(C)[CH:3]=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=[O:19].[C:20]12([C:27](=[O:28])[O:26]C1=O)[CH2:23][CH2:22][CH2:21]2>>[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([C:3]([C@H:23]3[CH2:22][CH2:21][C@H:20]3[C:27]([OH:26])=[O:28])=[O:4])=[CH:16][CH:17]=2)[CH2:12][C:11]1=[O:19]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 321710OxindoleHCID 6451240Aluminum(III) ChlorideHCID 10986226HCID 10986226, compound

Product 1

HCID 22827913HCID 22827913, compoundYield 94%

Procedure

20 ml (0.26 mole) of dimethylformamide are added dropwise to 120 g (0.9 mole) of anhydrous aluminum chloride in the course of a few minutes, while stirring, a highly exothermic reaction taking place. A mixture of 11.8 g (0.089 mole) of indolin-2-one and 11.3 g (0.09 mole) of cyclobutanedicarboxylic anhydride is then added a little at a time at 140° C., after which stirring is continued for a further 10 minutes at this temperature. The melt is then introduced into 0.5 kg of ice. The precipitated solid is filtered off under suction, and the aqueous phase is extracted several times with ethyl acetate. 21.7 g (93.6%) of cis-2-(indolin-2-on-5-oyl)-cyclobutanecarboxylic acid of melting point 211°-212° C. are obtained.

Workup

  1. customa highly exothermic reaction
  2. additionis then added a little at a time at 140° C.
  3. stirringafter which stirring
  4. filtrationThe precipitated solid is filtered off under suction
  5. extractionthe aqueous phase is extracted several times with ethyl acetate

Sources & evidence

ORD record
ord-8c9e72db987b4975811a320f79b76ff9
Source dataset
uspto-grants-1988_09
Patent number
US04772598

Reaction notes

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