Nitric Acid → HCID 13897642, compound

HRID 1861934Notes

Reaction equation

HRID 1861934 reaction equation
[CH3:1][C:2]([NH2:11])([CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH3:3].S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18].O>C(Cl)(Cl)Cl>[CH3:3][C:2]([NH2:11])([CH3:1])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([N+:17]([O-:19])=[O:18])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 4771Phentermine

Product 1

HCID 13897642HCID 13897642, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of phentermine (1.0 g) in chloroform (20 ml) was added dropwise to sulfuric acid (3.57 ml) at 0° C.; then fuming nitric acid (specific gravity=1.52; 2.8 ml) was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 2 h, made alkaline with water and a 2 N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=9:1) to give 367 mg of the titled compound (yield, 28%).

Workup

  1. extractiona 2 N aqueous sodium hydroxide solution and extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-f0eec02f926b4e148f7c0d012867de6f
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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