Hydrazine hydrate (1:1) → 6-Chloro-1,3-dihydroindol-2-one

HRID 1906571Notes

Reaction equation

HRID 1906571 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=O)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.O.NN.[O-]CC.[Na+]>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 2413316-Chloroindoline-2,3-dioneHCID 2723922Sodium ethoxide

Product 1

HCID 7363446-Chloro-1,3-dihydroindol-2-oneYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, mp 196°-198° C.

Sources & evidence

ORD record
ord-68e44a6fb7144ea287873776ac8965cf
Source dataset
uspto-grants-1987_03
Patent number
US04652658

Reaction notes

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