Hydroxyamine hydrochloride → 2,3-Dichloro-4-hydroxy-4'-fluorobenzophenone oxime

HRID 652881Notes

Reaction equation

HRID 652881 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[C:15]([OH:18])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=O.Cl.[NH2:20][OH:21]>N1C=CC=CC=1>[Cl:1][C:2]1[C:16]([Cl:17])=[C:15]([OH:18])[CH:14]=[CH:13][C:3]=1[C:4](=[N:20][OH:21])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 130157072,3-Dichloro-4-hydroxy-4'-fluorobenzophenone

Product 1

HCID 1363936812,3-Dichloro-4-hydroxy-4'-fluorobenzophenone oxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 35 g of 2,3-dichloro-4-hydroxy-4'-fluorobenzophenone in 250 ml pyridine, 34.6 g of hydroxylamine HCl is added. The mixture is refluxed for 4 hours. The pyridine is evaporated in vacuo. The residue is partitioned between 5% HCl and ethyl acetate. The ethyl acetate extract is washed with water, dried over Na2SO4 and evaporated to give 2,3-dichloro-4-hydroxy-4'-fluorobenzophenone oxime as a mixture of isomers, mp 150°-156° C.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. customThe pyridine is evaporated in vacuo
  3. customThe residue is partitioned between 5% HCl and ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washis washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-6cbf11b26530427a8609ce3708aa3542
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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