Nitrogen oxide (N2O4) → HCID 20333805, compound

HRID 614102Notes

Reaction equation

HRID 614102 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-2677743415d343369e02934c0ad17bd7
Source dataset
uspto-grants-1979_03
Patent number
US04143154

Reaction notes

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