Nitric Acid → 8-methoxy-5-nitro-3,4-dihydro-1(2H)-naphthalenone

HRID 1633722

Reaction equation

HRID 1633722 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][CH2:8]2.[N+:14]([O-])([OH:16])=[O:15].O>C(OC(=O)C)(=O)C.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:14]([O-:16])=[O:15])=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][CH2:8]2

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 112753358-Methoxy-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 111720678-methoxy-5-nitro-3,4-dihydro-1(2H)-naphthalenone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 8-methoxy-1-tetralone (2.26 g, 13 mmol) (prepared as described in Chatterjee, A. Tetrahedron, (1980), 36, 2513-2520) in acetic anhydride (11.5 mL) was cooled to 0° C., treated with a mixture of fuming nitric acid (0.90 mL) in acetic acid (0.70 mL) dropwise over 1 hour, stirred at 0° C. for 1.5 hours, treated with water (150 mL) and extracted with diethyl ether (300 mL). The diether ether layer was washed with water (150 mL), washed with sodium bicarbonate solution (3×), washed with brine, dried (MgSO4), filtered and concentrated. Purification of the residue on silica gel using a gradient of 2:1 and then 3:2 and finally 1:1 hexanes:ethyl acetate provided the desired product as the more polar isomer.

Workup

  1. extractionextracted with diethyl ether (300 mL)
  2. washThe diether ether layer was washed with water (150 mL)
  3. washwashed with sodium bicarbonate solution (3×)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue on silica gel using a gradient of 2:1

Sources & evidence

ORD record
ord-170144955c944271a0017f417eb4653c
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Linked notes

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