Hydrochloric Acid → (2Z)-2-hydroxyimino-5-methoxy-3H-inden-1-one

HRID 471809

Reaction equation

HRID 471809 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 6399792(2Z)-2-hydroxyimino-5-methoxy-3H-inden-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(methyloxy)-2,3-dihydro-1H-inden-1-one (1.0 g, 6.2 mmol) in methanol (15 mL) at 40° C. was added n-butyl nitrite (0.8 mL, 6.25 mmol) followed by conc HCl (0.6 mL). The reaction was stirred 30 min, precipitated solid was collected by filtration, air-dried and used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.60 (br.s, 2H) 3.86 (s, 3H) 6.99 (dd, J=8.54 Hz, 2.2 Hz, 1H) 7.12 (d, J=1.71 Hz, 1H) 7.66 (d, J=8.55 Hz, 1H) 12.45 (s, 1H).

Workup

  1. customprecipitated solid
  2. filtrationwas collected by filtration
  3. customair-dried
  4. customused without further purification

Sources & evidence

ORD record
ord-68ae70758fbe4de3bdd204d5e88e0f8f
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Linked notes

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