Hydroxyamine hydrochloride → HCID 178471206, compound

Temperature

80 °C

A mixture of 1,1-dimethylethyl 6-cyano-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 26; 533 mg, 1.38 mmol), hydroxylamine hydrochloride (575 mg, 8.27 mmol) and sodium bicarbonate (695 mg, 8.27 mmol) in ethanol (15 ml) was stirred at 80° C. for 32 h. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalent of each) were added, and heating was continued at 80° C. overnight. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalent of each) were added, and heating was continued at 80° C. for 5.5 h. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalent of each) were added, and heating was continued at 80° C. overnight. The mixture was cooled to room temperature and the solid was filtered off and washed with ethanol. The filtrate and washings were combined, most of the solvent removed, and the residue dissolved in ethyl acetate. The solution was washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (500 mg) as a pale yellow foam.

1. temperatureheating
2. waitwas continued at 80° C. overnight
3. temperatureheating
4. waitwas continued at 80° C. for 5.5 h
5. temperatureheating
6. waitwas continued at 80° C. overnight
7. temperatureThe mixture was cooled to room temperature
8. filtrationthe solid was filtered off
9. washwashed with ethanol
10. customremoved
11. dissolutionthe residue dissolved in ethyl acetate
12. washThe solution was washed with brine
13. dry with materialdried over MgSO4
14. concentrationconcentrated in vacuo

ORD record

ord-f986d637a14f46a185fb6eafe5726ecc

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263620B2