Hydrochloric Acid → 2-(Hydroxyimino)-N-[2-(propan-2-yl)phenyl]acetamide

HRID 2249549Notes

Reaction equation

HRID 2249549 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].[O-]S([O-])(=O)=O.[Na+].[Na+].Cl.Cl[C:20](Cl)(Cl)[CH:21]([OH:23])O.Cl.[NH2:27][OH:28]>O>[OH:28][N:27]=[CH:20][C:21]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[CH:1]([CH3:3])[CH3:2])=[O:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 125612-IsopropylanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 714439472-(Hydroxyimino)-N-[2-(propan-2-yl)phenyl]acetamideYield 60.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-isopropylaniline (4.7 g, 35 mmol), Na2SO4 (30.0 g), concentrated hydrochloride (3 mL), chloral hydrate (6.5 g), hydroxylamine hydrochloride (8.00 g) in water (150 mL) was heated at 85° C. for 40 minutes. After cooling to room temperature, it was extracted with ethyl acetate. The extracts were dried over magnesium sulfate and evaporated to dryness. Flash chromatography on silica gel provided 4.357 g (54%) of the title compound as solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionit was extracted with ethyl acetate
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-8937aaba98e449a3917e07fc5f6c0b7d
Source dataset
uspto-grants-2008_01
Patent number
US07314886B2

Reaction notes

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