Isatin → (3Z)-3-diazo-1H-indol-2-one

HRID 1156752Notes

Reaction equation

HRID 1156752 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-6010d29083f141fabfd887538404fe28
Source dataset
uspto-grants-1982_06
Patent number
US04337255

Reaction notes

Loading…