Dimethylformamide → HCID 22827913, compound

HRID 1632186Notes

Reaction equation

HRID 1632186 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, while stirring, to 120 g (0.9 mole) of anhydrous aluminum chloride in the course of a few minutes, whereupon a highly exothermic reaction starts. A mixture of 11.8 g (0.089 mole) of indolin-2-one and 11.3 g (0.09 mole) of cyclobutanedicarboxylic acid anhydride is then added a little at a time at 140° C., and stirring is continued at 140° C. and for 10 minutes. The melt is now poured onto 0.5 kg of ice, the solid precipitate is filtered off with suction and the aqueous phase is extracted several times with ethyl acetate to give 21.7 g (93.6%) of cis-2-(indolin-2-on-5-oyl)cyclobutanecarboxylic acid of melting point 211°-212° C.

Workup

  1. additionis then added a little at a time at 140° C.
  2. filtrationthe solid precipitate is filtered off with suction
  3. extractionthe aqueous phase is extracted several times with ethyl acetate

Sources & evidence

ORD record
ord-df512dffc3b9456aa2bc211fa2e09448
Source dataset
uspto-grants-1984_10
Patent number
US04474785

Reaction notes

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