Hydrochloric Acid → 2-Oximino-1-indanone

HRID 722270

Reaction equation

HRID 722270 reaction equation
[N:1](OCCC(C)C)=[O:2].[C:9]1(=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C:10]1=O.Cl.N([O-])=O>CO>[C:9]1(=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C:10]1=[N:1][OH:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 946NitriteHCID 8053Isoamyl NitriteHCID 1233581,2-Indandione

Product 1

HCID 63990382-Oximino-1-indanoneYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isoamyl nitrite (15 ml, 108 mmol) was added to a solution of indan-1,2-dione (12 g, 90 mmol) in MeOH (380 ml) at 45° C. followed by concentrated HCl (12 ml) dropwise over 5 minutes. The reaction mixture was stirred for 3 hours at room temperature. Excess isoaamyl nitrite (1 ml) and concentrated HCl (1 ml) was added and the suspension stirred for a further 15 minutes. On cooling to room temperature a white precipitate formed. The precipitate was filtered off and washed with cold MeOH (40 ml) followed by Et2O (40 ml) to afford indan-1,2-dione-2-oxime (6.2 g, 43%) as a white solid.

Workup

  1. stirringthe suspension stirred for a further 15 minutes
  2. temperatureOn cooling to room temperature a white precipitate
  3. customformed
  4. filtrationThe precipitate was filtered off
  5. washwashed with cold MeOH (40 ml)

Sources & evidence

ORD record
ord-b073b06a48e042f78d089e58073549e2
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Linked notes

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