Hydroxyamine hydrochloride → HCID 178438356, compound

Participants

Reaction Steps

4-[(3-n-propyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthyl)carbonyl]benzoic acid (101) (12.6 mmol) in EtOH (10 mL) and pyridine (15.3 mL) was treated with hydroxylamine hydrochloride (4.38 g, 63 mmol), and the mixture was heated at reflux. After 6 h, the mixture was cooled to room temperature and the ethanol was removed in vacuo. The residue was taken-up in water and the aqueous layer was adjusted to pH=4-5 with 1 M aqueous HCl. The aqueous solution was extracted with EtOAc, 3×. The organic layers were combined and washed with water (2×) and brine. The organic solution was dried (NaSO4), filtered, and concentrated to give a foamy white solid. Recrystallization (CH2Cl2/ether/hexanes) gave 4-[(3-n-propyl,5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbonyl]benzoic acid oxime (104), as white crystals (85%): mp 255-257°C.; 1H-NMR (400 MHz, CDCl3) δ8.19 (½ABq, J=8.3 Hz, 2H, ArH), 7.89 (½ABq, J=8.3 Hz, 2H, ArH), 7.23 (s, 1H, ArH), 7.20 (s, 1H, ArH), 2.65 (m, 2H, CH2), 1.70 (m, 4H, 2CH2), 1.56 (m, 2H, CH2), 1.32 (s, 6H, 2CH3) 1.20 (s, 6H, 2CH3), 0.88 (t, J=7.3 Hz, 3H, CH3).

Provenance & Evidence