Hydroxyamine hydrochloride → [o-(2,6-Dichloroanilino)-phenyl]-acetohydroxamic acid

HRID 46451Notes

Reaction equation

HRID 46451 reaction equation
[Na].Cl.N[OH:4].[Cl:5][C:6]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([NH2:18])=[O:17]>CO>[Cl:5][C:6]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([NH:18][OH:4])=[O:17]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 203870792-[2-(2,6-Dichloroanilino)phenyl]acetamide

Product 1

HCID 20300230[o-(2,6-Dichloroanilino)-phenyl]-acetohydroxamic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of 1.84 g of sodium in 80 ml of methanol is added, at 50°, a solution of 1.82 g of hydroxylamine hydrochloride in 30 ml of methanol. To the suspension is added, with stirring, a solution of 5.8 g of [o-(2,6-dichloroanilino)-phenyl]-acetamide (M.P. 188°-189°) in 80 ml of methanol, and the whole subsequently refluxed for 18 hours. After cooling, the red suspension is concentrated at 40° under 11 Torr to dryness. The residue is shaken with 600 ml of water and 100 ml of ether. The aqueous phase is separated and acidified with 2 N hydrochloric acid. The suspension is extracted with 200 ml of ether, the ether solution separated, washed with water, dried over magnesium sulphate, and concentrated at 40° under 11 Torr. The residue is crystallized from ether, whereby [o-(2,6-dichloroanilino)-phenyl]-acetohydroxamic acid is obtained, M.P. 164°-165°.

Workup

  1. additionTo the suspension is added
  2. temperatureAfter cooling
  3. concentrationthe red suspension is concentrated at 40° under 11 Torr to dryness
  4. stirringThe residue is shaken with 600 ml of water and 100 ml of ether
  5. customThe aqueous phase is separated
  6. extractionThe suspension is extracted with 200 ml of ether
  7. customthe ether solution separated
  8. washwashed with water
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated at 40° under 11 Torr
  11. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-94de997027694904b42dd88b9bb3fe59
Source dataset
uspto-grants-1979_11
Patent number
US04173577

Reaction notes

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