Pyridinium chloride → HCID 21459204, compound

HRID 1781805Notes

Reaction equation

HRID 1781805 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11](=[O:15])[CH2:12][CH2:13][CH3:14])=[CH:4][C:3]=1[O:16]C.Cl.N1C=CC=CC=1>Cl>[OH:16][C:3]1[CH:4]=[C:5]([C:11](=[O:15])[CH2:12][CH2:13][CH3:14])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 21459099HCID 21459099, compound

Product 1

HCID 21459204HCID 21459204, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

10.2 g of 4'-hydroxy-3'-methoxy-5'-nitrobutyrophenone are treated with 80 g of pyridine hydrochloride and stirred at 200° for 40 minutes. After cooling the reaction mixture is poured into 500 ml of ice-water. The mixture is treated with 30 ml of 3N hydrochloric acid and extracted with methylene chloride. The organic phase is dried over sodium sulfate and evaporated. The crude product obtained is chromatographed with methylene chloride on 150 g of silica gel. The material obtained is recrystallized from methylene chloride/n-hexane. There is obtained 3',4'-dihydroxy-5'-nitrobutyrophenone in the form of yellow crystals of m.p. 88°-90°.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customThe crude product obtained
  6. customis chromatographed with methylene chloride on 150 g of silica gel
  7. customThe material obtained
  8. customis recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-2e698d9c28294f70adc4c0cd77715ebf
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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