Hydroxylamine → 5,6-difluoro-2,3-dihydro-1H-indole-2,3-dione

HRID 414263Notes

Reaction equation

HRID 414263 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]([OH:14])O.NO.S(=O)(=O)(O)[OH:20]>>[F:9][C:8]1[CH:7]=[C:6]2[C:4](=[CH:3][C:2]=1[F:1])[NH:5][C:11](=[O:20])[C:12]2=[O:14]

Participants

5

Reactant 4

HCID 787HydroxylamineHCID 1118Sulfuric AcidHCID 2707Chloral HydrateHCID 774693,4-Difluoroaniline

Product 1

HCID 19263085,6-difluoro-2,3-dihydro-1H-indole-2,3-dione

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 3, gave 5,6-difluoroisatin, which was reacted with hydrazine hydrate followed by sodium methoxide in ethanol, in a manner analogous to Preparation 1, to give the title compound, m.p. 187°-190° C.

Workup

  1. customin a manner analogous to Parts A and B of Preparation 3

Sources & evidence

ORD record
ord-93eace560e5143b7b1075c0f9f7f7bca
Source dataset
uspto-grants-1988_12
Patent number
US04791131

Reaction notes

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