Hydroxyamine hydrochloride → HCID 66868365, compound

To a mixture of methyl 4-propionyl benzoic acid (0.50 g) and pyridine (5.0 mL) was added hydroxylamine hydrochloride (0.54 g) under ice-cooling, followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, to the residue were added ethyl acetate and a 10% aqueous citric acid solution and the aqueous layer was extracted with ethyl acetate. The organic layer was combined, and washed with a 10% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and to the residue was added ethanol (15 mL). To the reaction mixture were added a suspension of Raney nickel (2.0 mL) in ethanol (15 mL), and concentrated aqueous ammonia (3.0 mL), followed by stirring at room temperature for 14 hours under a hydrogen atmosphere of 3 atm. The insoluble materials in the reaction mixture were separated by filtration through Celite, and the filtrate was concentrated under reduced pressure. To the residue was added diethyl ether (10 mL), and a 4 M-hydrogen chloride/dioxane solution (1.0 mL) was added thereto under ice-cooling. The precipitated crystal was collected by filtration and washed with diethyl ether to obtain methyl 4-(1-amino propyl)benzoic acid hydrochloride (0.51 g).

1. temperaturecooling
2. concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
3. additionwere added ethyl acetate
4. extractiona 10% aqueous citric acid solution and the aqueous layer was extracted with ethyl acetate
5. washwashed with a 10% aqueous citric acid solution
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. additionto the residue was added ethanol (15 mL)
9. additionTo the reaction mixture were added
10. additiona suspension of Raney nickel (2.0 mL) in ethanol (15 mL), and concentrated aqueous ammonia (3.0 mL)
11. stirringby stirring at room temperature for 14 hours under a hydrogen atmosphere of 3 atm
12. customThe insoluble materials in the reaction mixture were separated by filtration through Celite
13. concentrationthe filtrate was concentrated under reduced pressure
14. additionTo the residue was added diethyl ether (10 mL)
15. additiona 4 M-hydrogen chloride/dioxane solution (1.0 mL) was added
16. temperatureunder ice-cooling
17. filtrationThe precipitated crystal was collected by filtration
18. washwashed with diethyl ether

ORD record

ord-8f4417e2b75f41fdb42c1feaba2b534e

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598355B2