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

HRID 2308724Notes

Reaction equation

HRID 2308724 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 9, gave 5,6-difluoroisatin, 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

Sources & evidence

ORD record
ord-5b738a436a2c418e88e938119d8a5b2f
Source dataset
uspto-grants-1987_09
Patent number
US04690943

Reaction notes

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