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

HRID 1580585Notes

Reaction equation

HRID 1580585 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 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-chloro-4-(p-methoxy)phenoxy-2-methyl-3-nitrosobutane (V) (4.803 g) in dry methanol (80 ml) was heated to reflux while ammonia gas was passed through until all the solid dissolved (3.5 h). Filtration and removal of solvents gave an off-white solid, which was largely freed of impurities by washing with benzene. Two recrystallisations from isopropanol (a small inorganic residue remained) gave the ketoxime hydrochloride (IV) (2.77 g, yield 53%) as colourless crystals, m.p. 219°-220° (decomp.).

Workup

  1. temperaturewas heated
  2. dissolutiondissolved (3.5 h)
  3. filtrationFiltration and removal of solvents
  4. customgave an off-white solid, which
  5. washby washing with benzene
  6. customTwo recrystallisations from isopropanol (a small inorganic residue

Sources & evidence

ORD record
ord-65e01234b61e4059b2ef6ebce0ad46a8
Source dataset
uspto-grants-1976_01
Patent number
US03933820

Reaction notes

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