Nitric Acid → HCID 22353182, compound

HRID 271104Notes

Reaction equation

HRID 271104 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[N+:23]([O-])([OH:25])=[O:24].O.[OH-].[Na+]>C(O)(=O)C>[N+:23]([C:5]1[CH:4]=[CH:3][C:2]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)=[C:1]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22983264-[3-(Biphenyl-2-yloxy)-propyl]-morpholine

Product 1

HCID 22353182HCID 22353182, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

4-[3-(Biphenyl-2-yloxy)-propyl]-morpholine (t, 500 mg, 1.46 mmol) was dissolved in 3 mL acetic acid and the reaction mixture was cooled in an ice bath. Concentrated nitric acid (3 mL) was added dropwise and the mixture was stirred for 15 minutes at 0° C., then at room temperature for one hour. The reaction was subsequently poured into 100 mL water and the pH of the reaction mixture was raised to >7 with 2N NaOH. The aqueous solution was extracted with ethyl acetate and dried. The solvent was then removed to afford 500 mg 4-[3-(5-nitro-biphenyl-2-yloxy)-propyl]-morpholine (u) which was used without further purification: m/e: 342.15, MS (ES+): 343.1; 1H NMR (500 MHz, CDCl3): 8.2-6.8 (m, 9H), 4.1 (m, 2H), 3.7 (m, 4H), 2.5 (m, 6H) and 1.8 (m, 2H).

Workup

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. waitat room temperature for one hour
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. customdried
  5. customThe solvent was then removed

Sources & evidence

ORD record
ord-0982b21f6d0c4deba14c7b98d6b0d334
Source dataset
uspto-grants-2008_11
Patent number
US07452873B2

Reaction notes

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