Isatin → (3Z)-3-diazo-1H-indol-2-one

HRID 65678Notes

Reaction equation

HRID 65678 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].C1(C)C=CC(S([NH:21][NH2:22])(=O)=O)=CC=1.[OH-].[Na+].[O-2].[Al+3].[O-2].[O-2].[Al+3]>>[N+:21](=[C:4]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][C:2]1=[O:3])=[N-:22]

Participants

5

Reactant 4

HCID 7054Isatin2×HCID 14798Sodium HydroxideHCID 15303P-ToluenesulfonylhydrazideHCID 9989226Alumina

Product 1

HCID 136455454(3Z)-3-diazo-1H-indol-2-one

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.

Workup

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

Sources & evidence

ORD record
ord-6b95a365086e4e3fa90b5593564ad1c0
Source dataset
uspto-grants-1978_12
Patent number
US04128644

Reaction notes

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