Reaction #93956

ord-6b95a365086e4e3fa90b5593564ad1c0

Reaction equation

O=C1Nc2ccccc2C1=O
isatin
O=C1Nc2ccccc2C1=O
isatin
Cc1ccc(S(=O)(=O)NN)cc1
p-toluenesulfonylhydrazine
[Na+].[OH-]
sodium hydroxide
[Al+3].[Al+3].[O-2].[O-2].[O-2]
aluminum oxide
→
[N-]=[N+]=C1C(=O)Nc2ccccc21
3-diazoindol-2(3H)-one

Reactants

O=C1Nc2ccccc2C1=O
isatin
O=C1Nc2ccccc2C1=O
isatin
Cc1ccc(S(=O)(=O)NN)cc1
p-toluenesulfonylhydrazine
—
hydrazone
[Na+].[OH-]
sodium hydroxide
[Al+3].[Al+3].[O-2].[O-2].[O-2]
aluminum oxide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe corresponding 3-diazoindol-2(3H)-one is prepared in accordance with known procedures

Procedure

Once the desired isatin has been obtained, the corresponding 3-diazoindol-2(3H)-one is prepared in accordance with known procedures. See, for example, J. M. Michowski, Tetrahedron Letters, 1773 (1967) and M. P. Cava, et al., J. Am. Chem. Soc., 80, 2257 (1958). The appropriate isatin compound is treated with p-toluenesulfonylhydrazine. The resulting hydrazone then is treated with a base such as aqueous sodium hydroxide or aluminum oxide to give the desired 3-diazoindol-2(3H)-one.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04128644uspto-grants-1978_12