HCID 20288518, compound → HCID 15634750, compound

HRID 126934Notes

Reaction equation

HRID 126934 reaction equation
[C:1]([C:9]1[C:10]([N+:22]([O-:24])=[O:23])=[C:11]([CH:15](C(O)=O)[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>S(=O)(=O)(O)O.C(O)(=O)C>[C:1]([C:9]1[C:10]([N+:22]([O-:24])=[O:23])=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 20288518HCID 20288518, compound

Product 1

HCID 15634750HCID 15634750, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 11.5 g (0.03 mole) of 2-(3-benzoyl-2-nitrophenyl)propanedioic acid in 50 ml of 20% sulfuric acid and 50 ml of acetic acid was heated at reflux under a nitrogen atmosphere overnight. The solution was concentrated and the residue was made basic with 450 ml of 2N potassium bicarbonate. The mixture was extracted twice with diethylether and the aqueous layer was made acidic with 20 ml of conc. sulfuric acid. The solid which precipitated was collected by filtration, washed with water, recrystallized from aqueous isopropanol to yield 4.1 g (48%) of brown solid, m.p. 160°-162° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere overnight
  2. concentrationThe solution was concentrated
  3. extractionThe mixture was extracted twice with diethylether
  4. customThe solid which precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customrecrystallized from aqueous isopropanol

Sources & evidence

ORD record
ord-e62666430c804499a9a350931d5207e2
Source dataset
uspto-grants-1981_03
Patent number
US04254146

Reaction notes

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