Pyridinium chloride → HCID 135609938, compound

HRID 1781904Notes

Reaction equation

HRID 1781904 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]([C:16]2[NH:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[O:15])[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C.Cl.N1C=CC=CC=1>>[OH:2][C:3]1[CH:4]=[C:5]([C:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[O:15])[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[OH:9]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 19000166HCID 19000166, compound

Product 1

HCID 135609938HCID 135609938, 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-ca378bffe04e423fa1b4aa032a117d2e
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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