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

HRID 1080422Notes

Reaction equation

HRID 1080422 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-ef72743a509f4846844579b2b75ec180
Source dataset
uspto-grants-1996_12
Patent number
US05580982

Reaction notes

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