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

HRID 263224Notes

Reaction equation

HRID 263224 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 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-chloro-4-(p-methyl)phenoxy-2-methyl-3-nitrosobutane (V) in dry methanol (120 ml) was heated to reflux and ammonia gas was passed through until all the solid dissolved (2 hours). Filtration and evaporation of solvent gave a brown solid, which was largely freed of impurities by washing with benzene. Recrystallisation from isopropanol (a small inorganic residue remained) gave the ketoxime hydrochloride (IV) (5.27 g, yield 66%) as colourless crystals, m.p. 217°-8° (decomp.).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. dissolutiondissolved (2 hours)
  4. filtrationFiltration and evaporation of solvent
  5. customgave a brown solid, which
  6. washby washing with benzene
  7. customRecrystallisation from isopropanol (a small inorganic residue

Sources & evidence

ORD record
ord-5612de6111174038b10c2041d6f52e8b
Source dataset
uspto-grants-1979_05
Patent number
US04156725

Reaction notes

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