O-Methylhydroxylamine → HCID 178502860, compound

HRID 1990746Notes

Reaction equation

[N:1]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH3:13][O:14][NH2:15]>C1(C)C=CC=CC=1.C(O)C.C(N(CC)CC)C.CO>[N:1]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]([NH:15][O:14][CH3:13])=[NH:10])=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: -10 °C

Procedure

4-Azidomethylbenzonitrile (17.3 g, 0.109 mol; Nishiyama et al; Chem. Lett. (1982) 1477) was dissolved in 500 mL of toluene and 200 mL of absolute ethanol. The solution was cooled to −10° C. and HCl(g) was bubbled through until saturation. The mixture was kept in the refrigerator for 2 days when most of the solvents were evaporated. Diethyl ether was added and was decanted off. The product was re-dissolved in a solution of O-methylhydroxylamine (10.5 g, 0.125 mol) and triethyl amine (56 mL) in 200 mL of methanol. The mixture was allowed to stand for 3 days whence the methanol was evaporated with addition of EtOAc. The organic phase was washed with water, dilute HOAc and aqueous sodium bicarbonate, dried (Na2SO4) and diluted with more EtOAc to a total volume of 500 mL. A sample of 25 mL was evaporated to dryness. The remainder was 932 mg. Total yield: 18.6 g (83%).

Workup

customHCl(g) was bubbled through until saturation
customwhen most of the solvents were evaporated
additionDiethyl ether was added
customwas decanted off
customwas evaporated with addition of EtOAc
washThe organic phase was washed with water, dilute HOAc and aqueous sodium bicarbonate
dry with materialdried (Na2SO4)
additiondiluted with more EtOAc to a total volume of 500 mL
customA sample of 25 mL was evaporated to dryness

Sources & evidence

ORD record: ord-3fd20192918a4d11b62468e0fe0a34a3
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645751B2

Reaction notes

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