Hydrochloric Acid → HCID 13986907, compound

HRID 579730Notes

Reaction equation

HRID 579730 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)/[CH:7]=[CH:8]/[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)([O-])=O.Cl.[H-].[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)/[CH:7]=[CH:8]/[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 166653HydrideHCID 53766177251-91-4

Product 1

HCID 13986907HCID 13986907, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An amount of 20.0 g of 2-(trans-3-nitrostyryl) quinoline was dissolved in 1000 ml of ethanol and 100 ml of conc. hydrochloric acid solution containing 49.0 g of stannous chloride.2 hydride was added thereto at room temperature, and the resulting mixture was refluxed for 5 hours. After the reaction mixture was cooled to room temperature, a 30% aqueous sodium hydroxide solution was added to regulate pH value to 13 and then the precipitated solid was collected by filtration and washed with water. After drying under reduced pressure, the precipitate was recrystallized from toluene to give 15.0 g (yield 84%) of the captioned compound as a pale yellowish white substance.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customAfter drying under reduced pressure
  5. customthe precipitate was recrystallized from toluene

Sources & evidence

ORD record
ord-67c4d1031735482693baca4360a91152
Source dataset
uspto-grants-1988_06
Patent number
US04749701

Reaction notes

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