Pyridinium chloride → HCID 10924607, compound

HRID 725410Notes

Reaction equation

HRID 725410 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11](=[O:21])[CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][C:3]=1[O:22]C.Cl.N1C=CC=CC=1>>[OH:22][C:3]1[CH:4]=[C:5]([C:11](=[O:21])[CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[OH:1]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 11823207HCID 11823207, compound

Product 1

HCID 10924607HCID 10924607, compound

Procedure

1.0 g of 4'-hydroxy-3'-methoxy-5'-nitro-4-phenylbutyrophenone is held at 200° for 1 hour with 8 g of pyridine hydrochloride. The reaction mixture is poured while still warm into ice-water and extracted with ethyl acetate. The organic phase is washed with 1N hydrochloric acid and subsequently with water, dried over sodium sulfate and evaporated. The dark residue obtained is chromatographed on a 30-fold amount of silica gel with ethyl acetate. From methylene chloride/hexane there is obtained 3',4'-dihydroxy-5'-nitro-4-phenylbutyrophenone in the form of yellow crystals of m.p. 118°-119°.

Workup

  1. additionThe reaction mixture is poured
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with 1N hydrochloric acid and subsequently with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe dark residue obtained
  7. customis chromatographed on a 30-fold amount of silica gel with ethyl acetate

Sources & evidence

ORD record
ord-4af32117574c4b7a8e33437f2048a9ea
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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