Nitric Acid → HCID 67325295, compound

HRID 1616898Notes

Reaction equation

HRID 1616898 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]1[CH:10]2[O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:9]2[CH2:8][CH2:7][N:6]1[C:18](=[O:20])[CH3:19]>O>[N+:1]([C:15]1[CH:16]=[CH:17][C:12]2[O:11][CH:10]3[CH2:5][N:6]([C:18](=[O:20])[CH3:19])[CH2:7][CH2:8][CH:9]3[C:13]=2[CH:14]=1)([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 67324329HCID 67324329, compound

Product 1

HCID 67325295HCID 67325295, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Fuming (90%) nitric acid (2.9 g) was added to 1-(3,4,4a,9a-tetrahydro-1H-benzo[4,5]furo[2,3-c]pyridin-2-yl)-ethanone (2.7 g, 12.5 mmol). The reaction mixture was stirred at 85° C. for 2 h, poured into H2O (350 mL) and the product was extracted with DCM (3×). The combined organic layers were washed with sodium hydrogenocarbonate and brine, and solvent was evaporated. Purification using silica gel chromatography (150 g SiO2) eluting with ethyl acetate yielded 1-(6-nitro-3,4,4a,9a-tetrahydro-1H-benzo[4,5]furo[2,3-c]pyridin-2-yl)-ethanone.

Workup

  1. extractionthe product was extracted with DCM (3×)
  2. washThe combined organic layers were washed with sodium hydrogenocarbonate and brine, and solvent
  3. customwas evaporated
  4. customPurification
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-231afde548f34bdfabc487bb0002e3d0
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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