Nitric Acid → 3,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-one

HRID 439340

Reaction equation

HRID 439340 reaction equation
[N+:1]([O-:4])(O)=[O:2].NC(N)=O.[CH3:9][C:10]1([CH3:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[CH2:11]1>>[CH3:9][C:10]1([CH3:20])[C:18]2[C:13](=[CH:14][C:15]([N+:1]([O-:4])=[O:2])=[CH:16][CH:17]=2)[C:12](=[O:19])[CH2:11]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1176UreaHCID 3046283,3-Dimethyl-1-indanone

Product 1

HCID 124417863,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-one

Conditions

Temperature
-10 °C

Procedure

A mixture of nitric acid (90% fuming, 35 mL) and urea (0.17 g) was cooled to -10° C. and purged with air for 20 minutes; 3,3-dimethyl-1-indanone (8.68 g, 54.2 mmoles) was added and the reaction was stirred for two hours at -10° C. to 5° C. The reaction mixture was poured into ice/H2O and extracted with ethyl acetate. The combined extracts were washed with distilled H2O, saturated NaHCO3 solution, saturated NaCl solution, and dried over MgSO4. The solvent was recovered under vacuum to obtain 10.0 g of a yellow solid. The crude product was recrystallized from methanol in two crops to obtain 8.08 g (71%) of the title D compound as yellow needles. MS: M- @ 205.

Workup

  1. custompurged with air for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with distilled H2O, saturated NaHCO3 solution, saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customThe solvent was recovered under vacuum

Sources & evidence

ORD record
ord-bff1c78e3d7947c5968302598b186785
Source dataset
uspto-grants-1996_05
Patent number
US05514690

Linked notes

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