Hydroxyamine hydrochloride → HCID 178501076, compound

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[N:19]N(C)C)=[O:12])[CH2:7][CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].Cl.NO>CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[O:12][N:19]=[C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:13]=23)[CH2:7][CH2:6]1)=[O:4]

Participants

Procedure

A mixture of trans-4-[2-(dimethyl-hydrazono)-cyclohexanecarbonyl]-cyclohexanecarboxylic acid methyl ester (0.95 g, 3.1 mmol), sodium acetate (0.28 g, 3.4 mmol) and hydroxylamine hydrochloride (0.24 g, 3.4 mmol) in methanol (15 ml) was stirred at room temperature for 16 h. The reaction mixture was partitioned between ethyl acetate (100 ml) and water (50 ml). The layers were separated. The aqueous layer was extracted with two 100-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue (0.88 g) was dissolved in toluene (15 ml). After addition of a catalytic amount of toluene-4-sulfonic acid monohydrate the mixture was heated at reflux for 3 h. The solvent was evaporated. Purification with n-heptane/ethyl acetate as eluent gave the title compound (0.58 g, 72%) with a regioisomeric purity of approx. 90% according to 13C-NMR. MS m/e: 264 ([M+H]+)