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

HRID 2249560Notes

Reaction equation

HRID 2249560 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH:15]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20])([CH3:17])[CH3:16].Cl.Cl.[NH2:27][OH:28]>O>[OH:28][N:27]=[CH:2][C:3]([NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=1[CH:15]([CH3:17])[CH3:16])=[O:5]

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 43.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 2-1 round-bottomed flask are placed water (1000 ml), followed by chloral hydrate (49 g, 0.30 mol), anhydrous sodium sulfate (225 g), 2-isopropylaniline (50 g, 0.37 mol), concentrated hydrochloric acid (22 ml, 0.26 mol), hydroxylamine hydrochloride (57 g, 0.81 mol). The solution was boiled for 3 hr, cooled, quenched with water, and extracted with ethyl acetate. The extracts were dried over MgSO4, and evaporated. The residue was purified by elution from a silica gel column with hexane/EtOAc (7:3) to afford the product (26.7 g, 35%). 1H NMR (300 MHz, CDCl3) δ 8.28 (br, NH), 7.88 (dd, 1H), 7.82 (b, NOH), 7.63 (s, N═CH), 7.24 (m, 3H), 3.04 (m, 1H), 1.27 (d, 6H); ESI (+) MS m/e=207 (MH+), ESI (−) MS m/e=205 (MH−).

Workup

  1. temperaturecooled
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extracts were dried over MgSO4
  5. customevaporated
  6. customThe residue was purified by elution from a silica gel column with hexane/EtOAc (7:3)

Sources & evidence

ORD record
ord-1de57bf158624e30a99edb20f024e6c5
Source dataset
uspto-grants-2008_01
Patent number
US07314886B2

Reaction notes

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