Dimethylformamide → 2-Methyl-6-nitrobenzaldoxime

HRID 1444928Notes

Reaction equation

CN(C=O)C.C[O-].[K+].[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[CH3:19])([O-:11])=[O:10].[N:20](OCCCC)=[O:21]>C(O)(=O)C.O>[CH3:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([N+:9]([O-:11])=[O:10])[C:13]=1[CH:19]=[N:20][OH:21]

Participants

Conditions

Temperature: -40 °C

Procedure

1200 ml of anhydrous DMF are initially charged in a 4 l reaction flask and cooled to −40° C. At this temperature, 336.5 g (4.56 mol) of potassium methoxide (95%) are added and suspended with stirring. A mixture of 300 g (1.92 mol) of 3-nitro-o-xylene (97%) and 274 g (2.52 mol) of n-butyl nitrite (95%) is then added dropwise at −40° C. over a period of 7 hours (if the mixture is cooled accordingly, the duration of this addition can be reduced as desired). The complete conversion of the starting material is checked by HPLC. The reaction discharge is then added with stirring, at from −5 to 0° C., to a mixture of 300 ml of water and 300 ml of glacial acetic acid. The reaction mixture is then poured onto 6 kg of ice-water and the solid is separated off by filtration and washed twice with in each case 500 ml of water.

Workup

additionis then added dropwise at −40° C. over a period of 7 hours (if the mixture
temperatureis cooled accordingly
additionthe duration of this addition
additionThe reaction discharge is then added
customthe solid is separated off by filtration
washwashed twice with in each case 500 ml of water

Sources & evidence

ORD record: ord-41efe65ce3714e9d8ee82191b0a1b7df
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07663001B2

Reaction notes

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