Hydrochloric Acid → HCID 6790533, compound

HRID 1762729Notes

Reaction equation

HRID 1762729 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].Cl.[NH2:11][OH:12].Cl.Cl[C:15](Cl)(Cl)[CH:16]([OH:18])O.S([O-])([O-])(=O)=O.[Na+].[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:16](=[O:18])[CH:15]=[N:11][OH:12])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 774693,4-DifluoroanilineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 6790533HCID 6790533, compound

Procedure

In accordance with the above reaction scheme, an aqueous solution of 3,4-difluoroaniline (I) and hydroxylamine hydrochloride containing hydrochloric acid is reacted with an aqueous solution of chloral hydrate and sodium sulfate at the reflux, then filtered while hot, giving N-(3,4-difluorophenyl)-2-(hydroxyimino)-acetamide (II). The compound (II) is reacted with concentrated sulfuric acid with heat, then added to cracked ice, giving 5,6-difluoro-1H-indole-2,3-dione (III). A basic aqueous solution of compound (III) is treated with hydrogen peroxide and heat, then cooled and acidified, giving 2-amino-4,5-difluorobenzoic acid (IV). The compound (IV) is added to a mixture of anhydrous copper(II) chloride, t-butyl nitrite and anhydrous acetonitrile at 0°-5° C., then added to a dilute mineral acid, giving 2-chloro-4,5-difluorobenzoic acid (V).

Workup

  1. customIn accordance with the above reaction scheme
  2. filtrationfiltered while hot,

Sources & evidence

ORD record
ord-201cadde04dc4c9086d651b19b9267e5
Source dataset
uspto-grants-1989_05
Patent number
US04833270

Reaction notes

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