Methane → Ethyl alpha-nitro-5H-dibenzo[a,d]cycloheptene-5-acetate

HRID 258198Notes

Reaction equation

HRID 258198 reaction equation
[CH:1]1[CH:15]=[C:14]2[C:4]([CH:5](O)[C:6]3[C:11]([CH:12]=[CH:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:3][CH:2]=1.[N+:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])([O-:19])=[O:18].C(OCC)C.C>CO>[N+:17]([CH:20]([CH:5]1[C:4]2[CH:3]=[CH:2][CH:1]=[CH:15][C:14]=2[CH:13]=[CH:12][C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 297MethaneHCID 3283Diethyl EtherHCID 69379Ethyl nitroacetateHCID 82577Dibenzosuberenol

Product 1

HCID 15290760Ethyl alpha-nitro-5H-dibenzo[a,d]cycloheptene-5-acetateYield 41.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

Dibenzosuberenol (42 g, 0.2 mol) is combined with ethyl nitroacetate (25 mL, 0.23 mol) and the mixture is heated at 120° C. (oil bath) until melted and then kept at 110° C. for 2.5 hours. The oil bath is removed and the cooled reaction mixture is dissolved in 50 mL of methanol and taken up into 350 mL of boiling diethyl ether. The dark solution is treated with charcoal, filtered, and cooled overnight. A precipitate is collected by filtration, washed with hexane, diethyl ether, dried under vacuum at room temperature to give 26.7 g of the title compound; mp 101°-103° C.

Workup

  1. customThe oil bath is removed
  2. customthe cooled reaction mixture
  3. filtrationfiltered
  4. temperaturecooled overnight
  5. filtrationA precipitate is collected by filtration
  6. washwashed with hexane, diethyl ether
  7. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-12017e8526524ccfa71bdf91106d4441
Source dataset
uspto-grants-1993_11
Patent number
US05264577

Reaction notes

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