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

HRID 568652Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH3:17])[C:10]=1[OH:18].Cl.[NH2:21][OH:22]>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[C:8](=[N:21]/[OH:22])/[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH3:17])[C:10]=1[OH:18]

Participants

Conditions

Temperature: 200 °C

Procedure

2'-fluoro-2-hydroxy-4-methoxy-3-methylbenzophenone (30.0 g) is refluxed 18 hours in 350 ml of pyridine containing 32.0 g of hydroxylamine hydrochloride. The solvent is removed in vacuo and the residue is distributed between ether and 5% HCl. Drying and concentration of the ether gives a crude product that is heated as a melt at 200° C. for 30 minutes in a nitrogen atmosphere. The melt is allowed to cool and the solid mass is triturated well with hexane to give E-2'-fluoro-2-hydroxy-4-methoxy-3-methylbenzophenone oxime, mp 167°-169° C.

Workup

customThe solvent is removed in vacuo
customDrying
customconcentration of the ether gives a crude product that
temperatureto cool
customthe solid mass is triturated well with hexane

Sources & evidence

ORD record: ord-4708c66f969a40c1901d9e878a7fa11e
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04728662

Reaction notes

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