1,4-Dioxane → HCID 54111985, compound

HRID 2352484Notes

Reaction equation

HRID 2352484 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:8]=[CH:7]2)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-].O1CCOCC1>O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH:14]=[CH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 6451240Aluminum(III) ChlorideHCID 54158128HCID 54158128, compound

Product 1

HCID 54111985HCID 54111985, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

41.6 g of 6-nitro-2-styrylquinoline were added in portions to a mixture containing 69 g of reduced iron, 6.9 g of aluminum chloride, 450 ml of dioxane, and 90 ml of water with heating under reflux. After heating under reflux for a further 5 hours, the solid was filtered using a Nutsche filter in which sellaite is laid. The filtrate was condensed, 130 ml of ethyl acetate were added thereto, and the deposited crystals were filtered. 28 g (74% of the theoretical yield) of the 6 -amino-2-styrylquinoline crystals were produced.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperatureAfter heating
  4. temperatureunder reflux for a further 5 hours
  5. filtrationthe solid was filtered
  6. filtrationfilter in which sellaite
  7. customcondensed, 130 ml of ethyl acetate
  8. additionwere added
  9. filtrationthe deposited crystals were filtered

Sources & evidence

ORD record
ord-eaf13cf623234272aecf240874fd8129
Source dataset
uspto-grants-1989_10
Patent number
US04877723

Reaction notes

Loading…