Dimethylformamide → 2-Methyl-6-nitrobenzaldoxime

HRID 49674

Reaction equation

HRID 49674 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

7

Reactant 4

HCID 6228DimethylformamideHCID 67391,2-Dimethyl-3-nitrobenzeneHCID 10996Butyl nitriteHCID 23664618Potassium methoxide

Product 1

HCID 853610482-Methyl-6-nitrobenzaldoxime

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

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 with stirring and suspended. 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 subsequently added dropwise at −40° C. over a period of 7 hours (if the mixture is cooled appropriately, the duration of this addition can be reduced at will). By HPLC, it is checked that the starting material has been converted completely. The reaction discharge is subsequently added with stirring to a mixture of 300 ml of water and 300 ml of glacial acetic acid, at from −5 to 0° C. The reaction mixture is then poured into 6 kg of ice-water and the solid is separated off by filtration and washed twice with 500 ml of water each time.

Workup

  1. additionis subsequently added dropwise at −40° C. over a period of 7 hours (if the mixture
  2. temperatureis cooled appropriately
  3. additionthe duration of this addition
  4. additionThe reaction discharge is subsequently added
  5. customthe solid is separated off by filtration
  6. washwashed twice with 500 ml of water each time

Sources & evidence

ORD record
ord-94daed2367de4fa094b6e9d6f1589599
Source dataset
uspto-grants-2004_03
Patent number
US06706886B2

Linked notes

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