Nitric Acid → HCID 15712739, compound

HRID 1195822Notes

Reaction equation

HRID 1195822 reaction equation
[CH:1]([CH:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)C>[CH:1]([CH:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15660880HCID 15660880, compound

Product 1

HCID 15712739HCID 15712739, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-isopropyl-7-phenylheptanoic acid (1.0 g; prepared as the intermediate for the compound of example 1 (b)) was dissolved in anhydrous acetic acid (5 ml). The solution was cooled in an ice-bath. Fuming nitric acid (0.4 ml) was dropped into the solution. The solution was stirred for 30 mins. Anhydrous acetic acid was quenched by adding potassium hydroxide to the reaction solution. The reaction solution adjusted to pH 6.0-7.0 was extracted with ethyl acetate. The ethyl acetate layer separated was washed with water, followed by saturated brine, dried and then evaporated. The residue was purified by column chromatography on silica gel to give the title compound (850 mg) having the following physical data:

Workup

  1. temperatureThe solution was cooled in an ice-bath
  2. customAnhydrous acetic acid was quenched
  3. additionby adding potassium hydroxide to the reaction solution
  4. extractionwas extracted with ethyl acetate
  5. customThe ethyl acetate layer separated
  6. washwas washed with water
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-caae0a168f8e482985788ad9ebf2bc5f
Source dataset
uspto-grants-1992_05
Patent number
US05112847

Reaction notes

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