Hydroxylamine → 5,6-Difluorooxindole

HRID 1382809Notes

Reaction equation

HRID 1382809 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].Cl[C:11](Cl)(Cl)[CH:12](O)[OH:13].NO.S(=O)(=O)(O)O.O.NN.C[O-].[Na+]>C(O)C>[F:9][C:8]1[CH:7]=[C:6]2[C:4](=[CH:3][C:2]=1[F:1])[NH:5][C:12](=[O:13])[CH2:11]2

Participants

8

Reactant 6

HCID 787HydroxylamineHCID 1118Sulfuric AcidHCID 2707Chloral HydrateHCID 24654Hydrazine hydrate (1:1)HCID 774693,4-DifluoroanilineHCID 10942334Sodium Methoxide

Product 1

HCID 125852825,6-Difluorooxindole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of 3,4-difluoroaniline with chloral hydrate and hydroxylamine followed cyclization with sulfuric acid, in a manner analogous to Parts A and B of Preparation 9, gave 5,6-difluoroisatic, which was reacted with hydrazine hydrate followed by sodium methoxide in ethanol, in a manner analogous to Preparation 7, to give the title compound, m.p. 187°-190° C.

Workup

  1. customin a manner analogous to Parts A and B of Preparation 9
  2. customgave 5,6-difluoroisatic

Sources & evidence

ORD record
ord-138d68d43e9744c5b497d3c9563345d8
Source dataset
uspto-grants-1989_02
Patent number
US04808601

Reaction notes

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