Methyl vinyl ketone → HCID 21437086, compound

HRID 2397190Notes

Reaction equation

HRID 2397190 reaction equation
Cl.Cl.N[C:4]1[C:5]([NH2:18])=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH:7]=[CH:8][C:9]=1[CH3:10].[CH3:19][C:20]([CH:22]=[CH2:23])=O>C(O)C.[Cl-].[Zn+2].[Cl-]>[CH3:19][C:20]1[C:4]2[C:5](=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]4[C:12]=3[N:18]=[CH:5][CH:4]=[C:9]4[CH3:8])[CH:7]=[CH:8][C:9]=2[CH3:10])[N:18]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 131710729HCID 131710729, compound

Product 1

HCID 21437086HCID 21437086, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 110 g (0.386 mol) of diaminodimethylbiphenyl dihydrochloride, 418 g (1.55 mol) of ferric chloride hexahydrate, and 10.2 g (0.075 mol) zinc chloride in 500 ml of 95% ethanol heated to 50° C. was added 55.6 g (0.78 mol) of methylvinyl ketone over a 90 minute period. The solution was refluxed for 2 hours then allowed to stand over night. Most of the ethanol was removed at reduced pressure and the residue made basic with 25% sodium hydroxide. The basic solution was evaporated to dryness and the dark residue was extracted four times with 400 ml portions of benzene. The extracts were evaporated to dryness to give a dark brown residue. Extraction of the residue with 150 ml of ethanol resulted in a light brown solid which was sublimed (250° C, 0.1 torr) to give 29 g (24%) of 4,4',5,5'-tetramethyl-8,8'-biquinoline, mp 290°-295° C. Crystallization from benzene/hexane afforded an analytical sample, mp 292°-295° C.

Workup

  1. temperatureThe solution was refluxed for 2 hours
  2. waitto stand over night
  3. customMost of the ethanol was removed at reduced pressure
  4. customThe basic solution was evaporated to dryness
  5. extractionthe dark residue was extracted four times with 400 ml portions of benzene
  6. customThe extracts were evaporated to dryness
  7. customto give a dark brown residue
  8. extractionExtraction of the residue with 150 ml of ethanol
  9. customresulted in a light brown solid which
  10. custom(250° C, 0.1 torr)

Sources & evidence

ORD record
ord-812caf1f0a584b15a2ef0175b7c59582
Source dataset
uspto-grants-1977_05
Patent number
US04021409

Reaction notes

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