Water → 2-Methyl-6-nitrobenzaldoxime

HRID 970150Notes

Reaction equation

HRID 970150 reaction equation
[N:1](OCCCC)=[O:2].[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[CH3:18])([O-:10])=[O:9].CC(C)([O-])C.[K+].O>CN(C)C=O.C(O)(=O)C>[CH3:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[C:12]=1[CH:18]=[N:1][OH:2]

Participants

7

Reactant 4

HCID 962WaterHCID 67391,2-Dimethyl-3-nitrobenzeneHCID 10996Butyl nitriteHCID 23665647Potassium tert-butoxide

Product 1

HCID 853610482-Methyl-6-nitrobenzaldoxime

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 274 g (2.6 mol) of n-butyl nitrite (97%) and 300 g (2.0 mol) of 3-nitro-o-xylene (97%) in 750 ml of dimethylformamide is cooled to from −55 to −60° C., and a solution of 522 g (4.56 mol) of potassium tert-butoxide in 750 ml of dimethylformamide is added dropwise at this temperature over a period of 2.5 hours. During the addition, the color of the solution changes from yellow to deep red and the solution becomes viscous. The reaction is monitored by HPLC. For work-up, initially 300 ml of water are added and then about 300 ml of glacial acetic acid, until the pH has reached 5-6. During the addition, the temperature increases to −10° C., and a yellow suspension is formed. The reaction mixture is then poured onto 6 kg of ice-water and the residue that has formed is filtered off with suction, washed with 5 l of water and dried in a drying cabinet at 30° C. overnight.

Workup

  1. additionDuring the addition
  2. additionDuring the addition
  3. customa yellow suspension is formed
  4. customthe residue that has formed
  5. filtrationis filtered off with suction
  6. washwashed with 5 l of water
  7. customdried in a drying cabinet at 30° C. overnight

Sources & evidence

ORD record
ord-47e84d28542844f095a5cf68ff451df8
Source dataset
uspto-grants-2007_12
Patent number
US07309802B2

Reaction notes

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