Hydrochloric Acid → 2-Hydroxyimino-N-indan-4-yl-acetamide

HRID 507063Notes

Reaction equation

HRID 507063 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].S(O)(O)(=O)=O.[NH2:20][OH:21].[NH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH2:25][CH2:26][CH2:27]2.Cl>O>[OH:21][N:20]=[CH:2][C:3]([NH:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH2:25][CH2:26][CH2:27]2)=[O:5]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 1225694-AminoindanHCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 727406282-Hydroxyimino-N-indan-4-yl-acetamideYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of chloral hydrate (5.46 g, 33 mmol) and anhydrous sodium sulfate (25.6 g, 180 mmol) in water (92 mL) add a mixture of hydroxylamine sulfate (25.6 g, 156 mmol), 4-aminoindane (4 g, 30 mmol), concentrated hydrochloric acid (3.1 mL) in water (30.8 mL). Heat the mixture up to 45° C. for 90 min, to 52° C. over 45 min and to 75° C. for 60 min. Cool the mixture to room temperature and filter the solid. Wash the solid with water and hexane. Dry the solid under vacuum to yield the title compound (5.54 g, 90%). MS (ES−): 203 (M−H).

Workup

  1. waitto 75° C. for 60 min
  2. temperatureCool the mixture to room temperature
  3. filtrationfilter the solid
  4. washWash the solid with water and hexane
  5. customDry the solid under vacuum

Sources & evidence

ORD record
ord-5698eb4ae42646b0a98745a51caaad1c
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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