Ammonia → 3-Amino-1-phenoxy-3-methylbutan-2-one oxime hydrochloride

HRID 1580587Notes

Reaction equation

HRID 1580587 reaction equation
[Cl:1][C:2]([CH3:15])([CH:4]([N:13]=[O:14])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:3].[NH3:16]>CO>[ClH:1].[NH2:16][C:2]([CH3:15])([CH3:3])[C:4](=[N:13][OH:14])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21316467(3-Chloro-3-methyl-2-nitrosobutoxy)benzene

Product 1

HCID 867329813-Amino-1-phenoxy-3-methylbutan-2-one oxime hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-chloro-4-(p-methoxy)phenoxy-2-methyl-3-nitrosobutane (V) (4.0 g) in methanol (approx. 80 ml) was refluxed while ammonia gas was bubbled through the suspension. Methanol was added occasionally to keep the volume of the solution approximately constant. After 6 hours the solution was evaporated and the residue, after washings with acetone, gave the ketoxime hydrochloride (IV) (3.2 g, yield 75%) as colourless crystals, m.p. 225°.

Workup

  1. customwas bubbled through the suspension
  2. additionMethanol was added occasionally
  3. customAfter 6 hours the solution was evaporated
  4. washthe residue, after washings with acetone

Sources & evidence

ORD record
ord-cee1c14c223b4782bb65aaebd0aed497
Source dataset
uspto-grants-1976_01
Patent number
US03933820

Reaction notes

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