HCID 20288513, compound → HCID 15634751, compound

HRID 126935Notes

Reaction equation

HRID 126935 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[C:9]([N+:21]([O-:23])=[O:22])=[C:10]([CH:14](C(O)=O)[C:15]([OH:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1>S(=O)(=O)(O)O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:9]([N+:21]([O-:23])=[O:22])=[C:10]([CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 20288513HCID 20288513, compound

Product 1

HCID 15634751HCID 15634751, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 6.9 g (0.017 mol) of 2-[3-(4-chlorobenzoyl)-2-nitrophenyl]propanedioic acid in 40 ml of 20% sulfuric acid and 40 ml of acetic acid was heated at reflux under a nitrogen atmosphere overnight. The reaction mixture was cooled, and the solid which precipitated was collected by filtration and stirred with 150 ml of 5% sodium bicarbonate. The mixture was filtered and the filtrate was made acidic with concentrated sulfuric acid. The resulting white solid was collected by filtration and recrystallized from aqueous isopropyl alcohol to yield 3.2 g (61%) of white needles, m.p. 164°-165° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere overnight
  2. temperatureThe reaction mixture was cooled
  3. customthe solid which precipitated
  4. filtrationwas collected by filtration
  5. filtrationThe mixture was filtered
  6. filtrationThe resulting white solid was collected by filtration
  7. customrecrystallized from aqueous isopropyl alcohol

Sources & evidence

ORD record
ord-7271f75ad0994b21ba967887bcfa14cb
Source dataset
uspto-grants-1981_03
Patent number
US04254146

Reaction notes

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