Acetic Anhydride → 6-Methoxy-5-nitro-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one

HRID 418956Notes

Reaction equation

HRID 418956 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.CC(OC(C)=O)=O.[N+:25]([O-])([OH:27])=[O:26].C(O)(=O)C>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]([N+:25]([O-:27])=[O:26])=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 110316906-methoxy-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-oneHCID 86584207Acetic acid nitric acid

Product 1

HCID 666522766-Methoxy-5-nitro-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-oneYield 34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 6-methoxy-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one (0.936 g, 4.06 mmol), Ac2O (5.0 mL), and a solution of 90% HNO3/acetic acid (0.8 mL), and stir under Nitrogen atmosphere at 0° C. After 3 hours, add ethyl acetate. Wash the ethyl acetate with sodium bicarbonate solution and then brine, dry over sodium sulfate, and concentrate in vacuum. Flash chromatograph using dichloromethane (isocratic) to yield the titled compound (0.378 g, 34%) as a solid. TLC Rf=0.25 in dichlormethane. 1H NMR (CDCl3): 8.22 (d, 1H, J=8.8 Hz), 7.04 (d, 1H, J=8.8 Hz), 3.99 (s, 3H), 2.96 (m, 2H), 2.49 (m, 2H), 1.63 (m, 8H).

Workup

  1. washWash the ethyl acetate with sodium bicarbonate solution
  2. dry with materialbrine, dry over sodium sulfate
  3. concentrationconcentrate in vacuum

Sources & evidence

ORD record
ord-a8f39b282df54ba9acbbb2d738341fed
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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