Hydrochloric Acid → 2-(Hydroxyimino)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

HRID 1952968Notes

Reaction equation

HRID 1952968 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2.[N:15](OCCC(C)C)=[O:16].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[C:7](=[N:15][OH:16])[CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 750185,6-Dimethoxy-1-indanone

Product 1

HCID 67540042-(Hydroxyimino)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5,6-Dimethoxy-1-indanone (0.078 moles, 15 g) is dissolved in absolute ethanol (550 ml), thermostated at 50° C., and added with isoamyl nitrite (0.086 moles, 11.9 ml) and conc. HCl (11.9 ml). After a few minutes the product precipitates. The reaction is kept at 50° C. for further 3 hours, then cooled at r.t. and the solid is filtered washing with absolute ethanol (50 ml) and ethyl ether (100 ml). The product is dried in oven under vacuum at r.t. Yield: 16.3 g (94.4%)

Workup

  1. customAfter a few minutes the product precipitates
  2. filtrationthe solid is filtered
  3. washwashing with absolute ethanol (50 ml) and ethyl ether (100 ml)
  4. customThe product is dried in oven under vacuum at r.t

Sources & evidence

ORD record
ord-d936209124fc4f798932fc5b440e1bda
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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