Isatin → (3Z)-3-diazo-1H-indol-2-one

HRID 2420368Notes

Reaction equation

HRID 2420368 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-76c5b1f4e45d4c11a05b91daff33b379
Source dataset
uspto-grants-1978_08
Patent number
US04110452

Reaction notes

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