Hydrochloric Acid → HCID 54148330, compound

HRID 2118951Notes

Reaction equation

HRID 2118951 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)=[CH:7][CH:6]=1)([O-])=O.C(O)C.[OH-].[K+]>[Fe].C(Cl)(Cl)Cl.O>[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 53983876HCID 53983876, compound

Product 1

HCID 54148330HCID 54148330, compoundYield 42.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

Hydrochloric acid (100 ml of 4N) is added dropwise to a mixture of 4-[2-(p-nitrophenyl)ethenyl]pyrimidine (28 g), ethanol (250 ml) and iron filings (28 g). The reaction temperature is increased to 65° C., and the mixture is stirred at that temperature for two hours. Water is added, followed by an aqueous 30% potassium hydroxide solution (200 ml), and chloroform (1 liter). The mixture is filtered through celite, and the chloroform layer is separated, dried over sodium sulfate and then concentrated. Addition of ether gives 4-[2-(p-aminophenyl)ethenyl]pyrimidine (10.3 g), m.p. 227°-230° C., which is used as the starting compound without further purification.

Workup

  1. filtrationThe mixture is filtered through celite
  2. customthe chloroform layer is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. additionAddition of ether

Sources & evidence

ORD record
ord-9a7f0d83ecac4c718395393d30677f25
Source dataset
uspto-grants-1987_07
Patent number
US04681884

Reaction notes

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