Hydroxyamine hydrochloride → (NZ)-N-[(4-chloro-2-fluoro-5-methoxyphenyl)-[4-(4-chlorophenoxy)-2-propylphenyl]methylidene]hydroxylamine

HRID 1172827Notes

Reaction equation

[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([Cl:23])=[CH:17][C:16]=3[F:24])=O)=[C:9]([CH2:25][CH2:26][CH3:27])[CH:8]=2)=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10](/[C:13](/[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([Cl:23])=[CH:17][C:16]=3[F:24])=[N:31]/[OH:32])=[C:9]([CH2:25][CH2:26][CH3:27])[CH:8]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the product from Step 3 (1.4 g, 3.2 mmol), hydroxylamine hydrochloride (2.2 g, 32 mmol) and sodium acetate (2.6 g, 32 mmol) in ethanol (30 mL) was stirred in a sealed tube at 60° C. for 72 h. The precipitate was filtered off and the filtrate was concentrated. The residue was purified by chromatography on silica gel to give the oxime product.

Workup

filtrationThe precipitate was filtered off
concentrationthe filtrate was concentrated
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-03cfe079c7e142128b5e3fbbf56af84c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834036B2

Reaction notes

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