Chloral Hydrate → HCID 6790533, compound

HRID 1762744Notes

Reaction equation

HRID 1762744 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[C:14](Cl)(Cl)[CH:15]([OH:17])O.S([O-])([O-])(=O)=O.[Na+].[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:15](=[O:17])[CH:14]=[N:11][OH:12])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

5

Reactant 4

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

Product 1

HCID 6790533HCID 6790533, compound

Procedure

A process for producing 2-chloro-4,5-difluorobenzoic acid which comprises reacting 3,4-difluoroaniline and hydroxylamine hydrochloride in an aqueous acidic solution with an aqueous solution of chloral hydrate and sodium sulfate at reflux, filtering while hot, giving N-(3,4-difluorophenyl)-2-(hydroxyimino)acetamide, which is reacted with concentrated sulfuric acid and heat, giving 5,6-difluoro-1H-indole-2,3-dione, which is dissolved in an aqueous base, treated with hydrogen peroxide and heat, then cooled and acidified, giving 2-amino-4,5-difluorobenzoic acid, which is reacted with anhydrous copper(II) chloride, t-butyl nitrite and anhydrous acetonitrile at 0°-5° C., then added to a dilute mineral acid, giving the desired compound.

Workup

  1. temperatureat reflux
  2. filtrationfiltering while hot,

Sources & evidence

ORD record
ord-6574f3f228cf4bb9bdeae237306d36ab
Source dataset
uspto-grants-1989_05
Patent number
US04833270

Reaction notes

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