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

HRID 568667Notes

Reaction equation

HRID 568667 reaction equation
[Cl:1][C:2]1[C:3]([OH:19])=[C:4]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])=O.Cl.[NH2:21][OH:22]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([OH:19])=[C:4]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])/[C:5](=[N:21]\[OH:22])/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 130157183-Chloro-2'-fluoro-2-hydroxy-4-methoxybenzophenone

Product 1

HCID 1364774092-chloro-6-[(E)-C-(2-fluorophenyl)-N-hydroxycarbonimidoyl]-3-methoxyphenol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-chloro-2'-fluoro-2-hydroxy-4-methoxybenzophenone (24.6 g) is refluxed for 18 hours in 300 ml of pyridine containing 12.2 g of hydroxylamine hydrochloride. The reaction mixture is concentrated under reduced pressure and is distributed between ether and 5% HCl. The organic phase is dried and evaporated and the resulting crystalline product fused at 205° C. for 45 minutes. The product is cooled and recrystallized from toluene to give E-3-chloro-2'-fluoro-2-hydroxy-4-methoxybenzophenone oxime, mp 184°-186° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe organic phase is dried
  3. customevaporated
  4. temperatureThe product is cooled
  5. customrecrystallized from toluene

Sources & evidence

ORD record
ord-dcc11ddf0f4a4239bc643c9e0b07ca2e
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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