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

HRID 2353932Notes

Reaction equation

HRID 2353932 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-ee3539f992164e7a821ff5cd03b4b015
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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