Hydrochloric Acid → 2-Hydroxyimino-N-indan-5-yl-acetamide

HRID 31358

Reaction equation

HRID 31358 reaction equation
Cl.Cl.[NH2:3][OH:4].[NH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH2:10][CH2:9]2.Cl[C:16](Cl)(Cl)[CH:17]([OH:19])O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O>[CH2:11]1[C:12]2[C:8](=[CH:7][C:6]([NH:5][C:17](=[O:19])[CH:16]=[N:3][OH:4])=[CH:14][CH:13]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 90496Indan-5-amineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 722820052-Hydroxyimino-N-indan-5-yl-acetamideYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

This compound is prepared according to the process described in Organic Syntheses, 1925, V, 71-74. A solution of 16.5 ml of concentrated HCl in 120 ml of water and a solution of 41.5 g of hydroxylamine hydrochloride in 70 ml of water are added to a mixture of 25 g of 5-aminoindane, 35 g of chloral hydrate and 22 g of Na2SO4 in 600 ml of water, and the mixture is then refluxed for 30 minutes. After cooling the reaction mixture to RT, it is extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is taken up in a pentane/iso ether mixture and the precipitate formed is spin-filtered off. 23 g of the expected product are obtained.

Workup

  1. customThis compound is prepared
  2. temperaturethe mixture is then refluxed for 30 minutes
  3. extractionit is extracted with EtOAc
  4. dry with materialthe organic phase is dried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. customthe precipitate formed
  7. filtrationis spin-filtered off

Sources & evidence

ORD record
ord-2870f34e8b1c47c59fdc29725e9d888c
Source dataset
uspto-grants-2008_09
Patent number
US07425566B2

Linked notes

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