Hydrochloric Acid → HCID 22922147, compound

HRID 2258518Notes

Reaction equation

HRID 2258518 reaction equation
[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:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.Cl.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[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:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 22922162HCID 22922162, compound

Product 1

HCID 22922147HCID 22922147, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-chloro-2-(5-nitrobenzofuran-2-yl)-quinoline (1.7 g), 10% aqueous hydrochloride (20 ml) and tin(II) chloride bihydrate (4.0 g) in ethanol (10 ml) was stirred mechanically under reflux for 7 hours. After being cooled, the resulting mixture was made basic with aqueous sodium hydroxide and filtered. The precipitates were dissolved into tetrahydrofuran (100 ml) and filtered. The filtrate was concentrated under reduced pressure to give crude materials, which were purified by column chlomatography to give 7-chloro-2-(5-aminobenzofuran-2-yl)quinoline (0.73 g).

Workup

  1. temperatureunder reflux for 7 hours
  2. temperatureAfter being cooled
  3. filtrationfiltered
  4. dissolutionThe precipitates were dissolved into tetrahydrofuran (100 ml)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give crude materials, which
  8. customwere purified by column chlomatography

Sources & evidence

ORD record
ord-266d5e8f526840f380e4df094952140d
Source dataset
uspto-grants-1997_08
Patent number
US05661159

Reaction notes

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