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

HRID 1080428Notes

Reaction equation

HRID 1080428 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].[K].[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([N+]([O-])=O)[CH:9]=1.O>CN(C)C=O>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67180Acetone, oximeHCID 969244-Chloro-2-nitrobenzonitrileHCID 5462222Potassium

Product 1

HCID 187964524-Chloro-2-[[(1-methylethylidene)amino]oxy]benzonitrileYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 75 ml of dry N,N-dimethylformamide was dissolved acetone oxime (1.21 g), followed by potassium tertiaryl butoxide (1.85 g) and stirred under nitrogen. After 30 minutes, 4-chloro-2-nitro-benzonitrile (2.00 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 the product, m.p. 83°-84° 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-6022ad05366d43928ae726c3e3c76203
Source dataset
uspto-grants-1996_12
Patent number
US05580982

Reaction notes

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