O-Methylhydroxylamine → HCID 178502860, compound
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-methylhydroxyl amine (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.
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
Sources & evidence
- ORD record
- ord-4b62ca25a18445cca3f8bb71f4f5cd6b
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129233B2
Reaction notes
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