Nitrogen oxide (N2O4) → 6,7-dihydro-2-nitro-3-phenyl-5H-indeno-[5,6-b]furan

HRID 443353

Reaction equation

HRID 443353 reaction equation
[C:1]1([C:7]2[C:8]3[CH:18]=[C:17]4[C:13]([CH2:14][CH2:15][CH2:16]4)=[CH:12][C:9]=3[O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:19]([O-:24])([N+]([O-])=O)=[O:20]>C(Cl)(Cl)Cl>[N+:19]([C:11]1[O:10][C:9]2[CH:12]=[C:13]3[C:17](=[CH:18][C:8]=2[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:16][CH2:15][CH2:14]3)([O-:24])=[O:20]

Participants

4

Reactant 2

HCID 25352Nitrogen oxide (N2O4)HCID 128663406,7-dihydro-3-phenyl-5 H-indeno-[5,6-b]furan

Product 1

HCID 128663396,7-dihydro-2-nitro-3-phenyl-5H-indeno-[5,6-b]furan

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.3 g. (0.01 mole) of the product of step B in 100 ml. of chloroform is added 1.8 g. (0.02 mole) of dinitrogen tetraoxide, and the mixture is stirred at about 20° C. for 20 hours. The mixture is evaporated, and the residue is triturated with isopropyl ether to provide a precipitate. The precipitate is separated by filtration and recrystallized from methanol to provide 6,7-dihydro-2-nitro-3-phenyl-5 H-indeno-[5,6-b]-furan, m.p. 161°-164° C.

Workup

  1. customThe mixture is evaporated
  2. customthe residue is triturated with isopropyl ether
  3. customto provide a precipitate
  4. customThe precipitate is separated by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-89b5ec3b4570457f85b41063207960c1
Source dataset
uspto-grants-1981_04
Patent number
US04260547

Linked notes

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