Hydrochloric Acid → HCID 6822331, compound

HRID 898871Notes

Reaction equation

HRID 898871 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[N:13](OCCCC)=[O:14].Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7](=[N:13][OH:14])[CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 787875-Methoxyindan-1-one

Product 1

HCID 6822331HCID 6822331, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 5-methoxyindan-1-one (75.8 g; 0.467 mol) in MeOH (1.4 L) at 45° C. is added butyl nitrite (81 mL; 0.693 mol) dropwise over 45 min. Concentrated HCl (45 mL) is then added to the hot solution over 20 min and the reaction was allowed to stir at 45° C. for an additional 1.5-2 h. The reaction suspension is cooled, the precipitate filtered, washed several times with cold MeOH, and dried under vacuo to afford 55.8 g (62%) of 5-methoxyindan-1,2-dione-2-oxime as a beige solid.

Workup

  1. temperatureThe reaction suspension is cooled
  2. filtrationthe precipitate filtered
  3. washwashed several times with cold MeOH
  4. customdried under vacuo

Sources & evidence

ORD record
ord-1fea71070c304e648a3137052ff10fff
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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