Water → 4-Methoxy-2-[[(1-methylethylidene)amino]oxy]benzonitrile

HRID 582866

Reaction equation

HRID 582866 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].[H-].[Na+].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([N+]([O-])=O)[CH:11]=1.O>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67180Acetone, oximeHCID 2886654-Methoxy-2-nitrobenzonitrile

Product 1

HCID 187964454-Methoxy-2-[[(1-methylethylidene)amino]oxy]benzonitrileYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of DMF was dissolved acetone oxime (0.74 g), followed by sodium hydride (0.30 g). After this mixture had stirred for 30 minutes, 4-methoxy-2-nitro-benzonitrile (1.50 g) was added. After an additional 30 minutes the reaction was poured into water (500 ml) and filtered. The solid was collected and dissolved in DCM (250 ml), dried (MgSO4), and concentrated in vacuo. The resulting solid was recrystallized from ethanol to yield 1.5 g of 4-methoxy-2-[[(1-methylethylidene)-amino]oxy]benzonitrile, m.p. 78-79° C.

Workup

  1. filtrationfiltered
  2. customThe solid was collected
  3. dissolutiondissolved in DCM (250 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-21a87d10fe224d3e99ec92abe84da1bb
Source dataset
uspto-grants-1999_07
Patent number
US05925766

Linked notes

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