Nitric Acid → 4-Hydroxy-3-methoxy-5-nitrophenyl (3-quinolinyl) ketone

HRID 2254806Notes

Reaction equation

HRID 2254806 reaction equation
[N+:1]([O-:4])(O)=[O:2].[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([O:24][CH3:25])[CH:18]=2)=[O:16])[CH:6]=1>C(O)(=O)C>[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:15]([C:17]2[CH:22]=[C:21]([N+:1]([O-:4])=[O:2])[C:20]([OH:23])=[C:19]([O:24][CH3:25])[CH:18]=2)=[O:16])[CH:6]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19000165HCID 19000165, compound

Product 1

HCID 190001534-Hydroxy-3-methoxy-5-nitrophenyl (3-quinolinyl) ketone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 1.91 ml of 65 percent nitric acid in 20 ml of glacial acetic acid is added dropwise to a solution of 5.5 g of 4-hydroxy-3-methoxyphenyl (3-quinolinyl) ketone in 300 ml of glacial acetic acid at 150° and the mixture is then stirred at this temperature for an additional 2 hours. The mixture is then poured into ice-water and extracted three times with 300 ml of ethyl acetate each time. The organic phase is washed five times with 100 ml of water each time, dried over sodium sulfate and evaporated. After treatment of the residue with ethyl acetate, there is obtained 4-hydroxy-3-methoxy-5-nitrophenyl (3-quinolinyl) ketone in the form of yellow crystals of m.p. 220°-221° (dec.).

Workup

  1. extractionextracted three times with 300 ml of ethyl acetate each time
  2. washThe organic phase is washed five times with 100 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-8df3fbe92e3e4902b408b7be1d74fef0
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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