Hydroxyamine hydrochloride → HCID 86753145, compound

HRID 2395036Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:8]([CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH2:22][CH2:23][OH:24])=[O:20])=[CH:15][CH:14]=2)[CH:9]=1)(=O)[CH3:2].Cl.[NH2:34][OH:35]>N1C=CC=CC=1>[CH2:26]([O:25][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[N:34][OH:35])[CH3:2])=[CH:9][C:8]=1[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH2:22][CH2:23][OH:24])=[O:20])=[CH:15][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-[3-(5-acetyl-2-benzyloxyphenyl)propyl]-N-(2-hydroxyethyl)benzenecarboxamide (0.5 g) (example 2, compound 45) hydroxylamine hydrochloride (0.16 g) in pyridine (5 ml) was heated at 60° C. for 2 hours. The pyridine was removed and the residue subjected to flash chromatography on silica, eluting with a mixture of ethyl acetate/hexane (4:1 v/v) to yield in the appropriate fractions, 4-[3-(2-benzyloxy-5-(1-hydroxyiminoethyl)phenyl)propyl]-N-(2-hydroxyethyl)benzenecarboxamide (m.p. 131°-2° C.; yield 56%).

Workup

customThe pyridine was removed
washeluting with a mixture of ethyl acetate/hexane (4:1 v/v)

Sources & evidence

ORD record: ord-b80a45033c34491aa4e0f5ff47245bb0
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811459

Reaction notes

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