Nitric Acid → HCID 22247322, compound

HRID 1107977Notes

Reaction equation

HRID 1107977 reaction equation
[CH2:1]([N:9]1[C:18]2[C:13](=[C:14]([CH3:26])[C:15]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:16]([CH3:19])[CH:17]=2)[CH2:12][CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[N+:27]([O-])([OH:29])=[O:28].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[CH2:1]([N:9]1[C:18]2[C:13](=[C:14]([CH3:26])[C:15]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:16]([CH3:19])[C:17]=2[N+:27]([O-:29])=[O:28])[CH2:12][CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 22247318HCID 22247318, compound

Product 1

HCID 22247322HCID 22247322, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

1-Octyl-6-ethoxycarbonylmethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline (1.0 g) was dissolved in acetic anhydride (5 ml), and a solution of 70% nitric acid (517 mg) in acetic anhydride (3 ml) was dropwise added, which was followed by stirring at the same temperature for 0.5 hr. The reaction mixture was poured into ice water (50 ml), neutralized with saturated aqueous solution of sodium hydrogencarbonate, and extracted with chloroform (50 ml). After washing with water, the chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane-ethyl acetate/n-hexane=1/5) to give 700 mg of oily 1-octyl-6-ethoxycarbonylmethyl-5,7-dimethyl-8-nitro-1,2,3,4-tetrahydroquinoline.

Workup

  1. extractionextracted with chloroform (50 ml)
  2. washAfter washing with water
  3. dry with materialthe chloroform layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: n-hexane-ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-20184ff8946b4d7aabeeda24e1f579bd
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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