Hydrochloric Acid → HCID 54366659, compound

HRID 1762069Notes

Reaction equation

HRID 1762069 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[CH:6][CH:5]=1)([O-])=O.CN(C=O)C.Cl.[OH-].[Na+]>[Fe].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17][C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 54309857HCID 54309857, compound

Product 1

HCID 54366659HCID 54366659, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

11.28 g of the 1,8-bis(4-nitrophenyl)-1,3,5,7-octatetraene synthesized in Synthesis Example 1 was added to 250 ml of DMF. To this mixture, 22.5 g of iron powder was added, and then diluted hydrochloric acid consisting of 5.6 ml of concentrated hydrochloric acid and 19 ml of water was added with stirring. The mixture was further stirred at 80~88° C. for 5 hours. The reaction mixture was cooled to 50° C. and was made alkaline by addition of a 10% aqueous solution of sodium hydroxide. Celite was added to the reaction mixture, and then insoluble components were filtered out, together with the Celite, from the reaction mixture, while it was hot. The filterate was diluted with water. As a result, crystals separated out. The crystals were filtered off, washed with water and dried, so that a crude diamino product was obtained. The product was recrystallized from a mixed solvent of DMF and water, whereby 1,8-bis(4-aminophenyl)-1,3,5,7-octatetraene was obtained in the form of dark red plate crystals. The melting point was 262.5~264.5° C.

Workup

  1. additionwas added
  2. stirringThe mixture was further stirred at 80~88° C. for 5 hours
  3. additionCelite was added to the reaction mixture
  4. filtrationinsoluble components were filtered out, together with the Celite, from the reaction mixture, while it
  5. additionThe filterate was diluted with water
  6. customAs a result, crystals separated out
  7. filtrationThe crystals were filtered off
  8. washwashed with water
  9. dry with materialdried, so that a crude diamino product
  10. customwas obtained
  11. customThe product was recrystallized from a mixed solvent of DMF and water

Sources & evidence

ORD record
ord-e7a778f3a4be45f9adf8eaef1cf2be57
Source dataset
uspto-grants-1989_05
Patent number
US04830943

Reaction notes

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