Pyridinium chloride → 7-Chloro-2-(5-formylbenzofuran-2-yl)quinoline

HRID 2258510Notes

Reaction equation

HRID 2258510 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][C:15]=3[CH:22]=O)=[N:9]2)=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][C:15]=4[CH:22]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 229221677-Chloro-2-(2,4-diformylphenoxymethyl)-quinoline

Product 1

HCID 229221457-Chloro-2-(5-formylbenzofuran-2-yl)quinolineYield 86.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7-chloro-2-(2,4-diformylphenoxymethyl)-quinoline (5.7 g) and pyridine hydrochloride (11.4 g) in toluene (140 ml) was stirred under reflux for 2 hours. After being cooled, the appeared crystals were collected, washed with toluene and water. The resulting crystals were washed with ethanol (100 ml) and dried to give 7-chloro-2-(5-formylbenzofuran-2-yl)quinoline (4.67 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter being cooled
  3. customthe appeared crystals were collected
  4. washwashed with toluene and water
  5. washThe resulting crystals were washed with ethanol (100 ml)
  6. customdried

Sources & evidence

ORD record
ord-86d6034f63b34dd990601a7fa48b1036
Source dataset
uspto-grants-1997_08
Patent number
US05661159

Reaction notes

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