Pyridinium chloride → HCID 91869294, compound

HRID 2260310Notes

Reaction equation

HRID 2260310 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10]1[C:15]([O:16]C)=[C:14]([O:18]C)[C:13]([N+:20]([O-:22])=[O:21])=[CH:12][C:11]=1[C:23]([C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[C:28]([O:34]C)=[C:27]([O:36]C)[C:26]=1[C:38]1[NH:39][C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=1)=[O:24].Cl.N1C=CC=CC=1>>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10]1[C:15]([OH:16])=[C:14]([OH:18])[C:13]([N+:20]([O-:22])=[O:21])=[CH:12][C:11]=1[C:23]([C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[C:28]([OH:34])=[C:27]([OH:36])[C:26]=1[C:38]1[NH:39][C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=1)=[O:24]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 86749164HCID 86749164, compound

Product 1

HCID 91869294HCID 91869294, compound

Procedure

1.0 g of 2-benzimidazolyl(3,4-dimethoxy-5-nitrophenyl)ketone and 8.0 g of pyridine hydrochloride are held at 200° for 60 minutes. The dark solution is poured while still warm into ice-water and extracted three times with 100 ml of ethyl acetate each time. The organic phase is washed with water, dried over sodium sulfate and evaporated. After recrystallization from ethyl acetate/hexane, there is obtained 2-benzimidazolyl(3,4-dihydroxy-5-nitrophenyl)ketone in the form of yellow crystals of m.p. 249°-250°.

Workup

  1. additionThe dark solution is poured
  2. extractionextracted three times with 100 ml of ethyl acetate each time
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customAfter recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e7b1747953614d99803af17d4e8802c2
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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