Hydrochloric Acid → HCID 53674338, compound

HRID 366974Notes

Reaction equation

HRID 366974 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][CH:22]=[CH:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)=[CH:16][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O.CN(C)C=O.Cl.[OH-].[Na+]>O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][CH:22]=[CH:23][C:24]3[CH:25]=[CH:26][C:27]([NH2:30])=[CH:28][CH:29]=3)=[CH:16][CH:15]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 54276481HCID 54276481, compound

Product 1

HCID 53674338HCID 53674338, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

21.22 g of 1,4-bis[4-(4-nitrophenyl)-1,3-butadienyl]benzene was put into 800 ml of dimethylformamide (DMF). To this mixture, 33.51 g of iron powder and an aqueous solution of hydrochloric acid prepared by diluting 8.5 ml of concentrated hydrochloric acid with 28 ml of water were successively added with stirring, and the obtained mixture was further stirred at 95 to 102° C. for 4 hours. The resultant mixture was cooled to 90° C., and adjusted to pH 9 by the addition of a 40% aqueous solution of sodium hydroxide. Thereafter, the insoluble matter was removed from the mixture by filtration using Celite™. The filtrate was concentrated to about 400 ml under reduced pressure. With the addition of 20 ml of water, the concentrated filtrate was cooled to room temperature. The separating crystals were collected by filtration, and successively washed with water and methanol, and heated with the application of heat under reduced pressure, whereby 13.40 g of mud yellow crystals was obtained in a 73.5% yield.

Workup

  1. additionwere successively added
  2. stirringthe obtained mixture was further stirred at 95 to 102° C. for 4 hours
  3. customThereafter, the insoluble matter was removed from the mixture by filtration
  4. concentrationThe filtrate was concentrated to about 400 ml under reduced pressure
  5. additionWith the addition of 20 ml of water
  6. filtrationThe separating crystals were collected by filtration
  7. washsuccessively washed with water and methanol
  8. temperatureheated with the application
  9. temperatureof heat under reduced pressure, whereby 13.40 g of mud yellow crystals
  10. customwas obtained in a 73.5% yield

Sources & evidence

ORD record
ord-44ef2b4f39ae477d9e17ef06f29825a3
Source dataset
uspto-grants-2000_10
Patent number
US06132914

Reaction notes

Loading…