Hydroxyamine hydrochloride → HCID 18923777, compound

HRID 1379689Notes

Reaction equation

HRID 1379689 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH:16]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH2:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:38]O>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[CH:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[N:38]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 18923786HCID 18923786, compound

Product 1

HCID 18923777HCID 18923777, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 1-(4-benzyloxyphenyl)-2-(4-methoxyphenyl)-5-(4-fluorophenyl)pentan-1,5-dione (1.0 g, 2.4 mmol) and hydroxylamine hydrochloride (0.2 g, 2.9 mmol) were refluxed in 30 mL of MeOH for 48 h, worked up, and purified to give 0.45 g (40 % yield) of product: mp 114°-115° C.; 1H NMR (CDCl3) d 3.82 (s, 3H, OCH3), 5.06 (s, 2H, OCH2Ar), 6.83-6.89 (m, 4H, ArH), 7.13-7.19 (m, 4H, ArH), 7.34-7.44 (m, 7H, ArH), 7.65-7.74 (dd, 2H, J=8, ArH), 8.10-8.14 (m, 2H, ArH); MS(FD) 461(M+). Anal. Calcd for C31H24NO2F: C, 80.67; H, 5.24; N,3.03. Found: C, 80.87; H, 5.30; N, 3.09.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-60f99dfd0dc641ee82308a4cdb06c481
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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