Pyridinium chloride → HCID 21459153, compound

HRID 274446Notes

Reaction equation

HRID 274446 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])=[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])[CH:12]([CH3:13])[CH3:14])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 21459100HCID 21459100, compound

Product 1

HCID 21459153HCID 21459153, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

8.0 g of 4'-hydroxy-3'-methoxy-2-methyl-5'-nitropropiophenone are treated with 64 g of pyridine hydrochloride and stirred at 180° for 45 minutes. After cooling the reaction mixture is poured into 500 ml of ice-water, whereupon it is made acid with 20 ml of 3N hydrochloric acid and extracted with methylene chloride. The organic phase is washed with water, dried over sodium sulfate and evaporated in a water-jet vacuum. After crystallization from methylene chloride/n-hexane there is obtained 3',4'-dihydroxy-2-methyl-5'-nitropropiophenone in the form of yellow crystals of m.p. 98°-99°.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with methylene chloride
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in a water-jet vacuum
  6. customAfter crystallization from methylene chloride/n-hexane there

Sources & evidence

ORD record
ord-a1f7b1a64d9d49709b19cd2792edc55a
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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