Hydrochloric Acid → 4-[2-(p-Aminophenyl)-ethenyl]-2-aminopyrimidine

HRID 476873Notes

Reaction equation

HRID 476873 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]=[C:15]([NH2:19])[N:14]=2)=[CH:7][CH:6]=1)([O-])=O.C(O)C.[OH-].[Na+]>[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]=[C:15]([NH2:19])[N:14]=2)=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 537919064-[2-(4-Nitrophenyl)ethenyl]pyrimidin-2-amine

Product 1

HCID 538590424-[2-(p-Aminophenyl)-ethenyl]-2-aminopyrimidine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

Hydrochloric acid (100 ml of 4N) is added dropwise to a stirred mixture of 4-[2-(p-nitrophenyl)-ethenyl]-2-aminopyrimidine (21.8 g), ethanol (250 ml) and iron filing (22 g). During the addition the reaction temperature is increased to 65° C., and stirring is continued (2 hours) at 65° C. Water is added, followed by an aqueous 30% sodium hydroxide solution (200 ml) and chloroform (1 liter). The chloroform layer is then separated and dried over sodium sulfate. After evaporation and addition of ether, 4-[2-(p-aminophenyl)-ethenyl]-2-aminopyrimidine is obtained (13.5 g), which is used as the starting compound without further purification.

Workup

  1. additionDuring the addition the reaction temperature
  2. custom(2 hours)
  3. customat 65° C
  4. customThe chloroform layer is then separated
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporation and addition of ether

Sources & evidence

ORD record
ord-025ea991ac3143c8a2a2165b6a819ee0
Source dataset
uspto-grants-1989_12
Patent number
US04886801

Reaction notes

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