Nitrogen oxide (N2O4) → HCID 20333805, compound

HRID 1706655Notes

Reaction equation

HRID 1706655 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[C:16]([CH2:19][C:20]([OH:22])=[O:21])[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[N+:23]([O-:28])([N+]([O-])=O)=[O:24]>C(#N)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[C:16]([CH2:19][C:20]([OH:22])=[O:21])[CH:17]=[CH:18][C:13]=3[O:12][C:11]=2[N+:23]([O-:28])=[O:24])=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 25352Nitrogen oxide (N2O4)2×HCID 20333807HCID 20333807, compound

Product 1

HCID 20333805HCID 20333805, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of 2 g. of the product of step B in 10 ml. of acetonitrile is added 0.2 g. of cupric nitrate hydrate and 1 g. of dinitrogen tetraoxide in 2 ml. of acetonitrile. The mixture is stirred at 20° C. for two hours, 0.5 g. of additional dinitrogen tetraoxide is added, and the mixture is stirred for an additional 18 hours. It is then concentrated, and the solid is separated by filtration and recrystallized from acetic acid to provide light yellow crystals of 3-(4-carboxyphenyl)-2-nitrobenzofuran-5-acetic acid, m.p. 290° C. (dec.).

Workup

  1. additionTo a suspension of 2 g
  2. stirringthe mixture is stirred for an additional 18 hours
  3. concentrationIt is then concentrated
  4. customthe solid is separated by filtration
  5. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-b142ea3f58a7430ab5958bb1480d52b7
Source dataset
uspto-grants-1980_06
Patent number
US04208335

Reaction notes

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