Pyridinium chloride → HCID 21459153, compound

HRID 725311Notes

Reaction equation

HRID 725311 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-2dc4b1cbc2d8473080e77f02c4d6d3fa
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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