Hydroxyamine hydrochloride → 2-chloro-6-[(E)-C-(2,5-difluorophenyl)-N-hydroxycarbonimidoyl]-3-methoxyphenol

HRID 652900Notes

Reaction equation

HRID 652900 reaction equation
[Cl:1][C:2]1[C:3]([OH:20])=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:5]([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[F:14])=O.Cl.[NH2:22][OH:23]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([OH:20])=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])/[C:5](=[N:22]\[OH:23])/[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[F:14]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 140125663-Chloro-2',5'-difluoro-2-hydroxy-4-methoxybenzophenone

Product 1

HCID 1364773902-chloro-6-[(E)-C-(2,5-difluorophenyl)-N-hydroxycarbonimidoyl]-3-methoxyphenol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 28 g of 3-chloro-2',5'-difluoro-2-hydroxy-4-methoxybenzophenone and 26 g of hydroxylamine HCl in 250 ml pyridine is refluxed for three hours. Pyridine is evaporated and the residue partitioned between ethyl acetate and 5% HCl. The ethyl acetate extract is washed with water, dried over Na2SO4 and evaporated to give a solid product as a mixture of isomers. The solid is heated at 200°-210° C. for approximately 30-45 minutes and recrystallized from toluene giving E-3-chloro-2',5'-difluro-2-hydroxy-4-methoxybenzophenone oxime, mp 209°-210° C.

Workup

  1. temperatureis refluxed for three hours
  2. customPyridine is evaporated
  3. customthe residue partitioned between ethyl acetate and 5% HCl
  4. extractionThe ethyl acetate extract
  5. washis washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto give a solid product
  9. additionas a mixture of isomers
  10. temperatureThe solid is heated at 200°-210° C. for approximately 30-45 minutes
  11. customrecrystallized from toluene

Sources & evidence

ORD record
ord-06cde5978e1f47528e2b59916958ec51
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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