Ethylene Glycol → 2-(1,1'-Biphenyl-4-yl)-1,2,4-triazole(5,1-a)isoquinoline

HRID 1446806Notes

Reaction equation

HRID 1446806 reaction equation
[Na].[NH2:2][N:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=O.[C:14]1([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)CO>C(O)C>[C:20]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:21]=[CH:22][C:23]([C:24]2[N:25]=[C:4]3[C:5]4[C:10]([CH:11]=[CH:12][N:3]3[N:2]=2)=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 18021(1,1'-Biphenyl)-4-carbonitrileHCID 5360545SodiumHCID 123832182-Amino-1(2H)-isoquinolinone

Product 1

HCID 1600732-(1,1'-Biphenyl-4-yl)-1,2,4-triazole(5,1-a)isoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution prepared from 0.075 g. of sodium dissolved in 20 ml of absolute ethanol was added to a suspension of 0.640 g. (0.004 mole) of 2-amino-isoquinoline-1(2H)-one and 0.720 g. (0.004 mole) of 4-phenyl-benzonitrile in 20 ml of absolute ethanol. The resulting mixture was refluxed for 30 minutes on an oil bath, then 15 ml. of ethylene glycol were added and the ethanol was distilled off by adjusting the temperature of the oil bath at about 150° C. After three hours the reaction mixture was cooled to room temperature whereby the title compound crystallized out. It was recovered by filtration and re-crystallized from a mixture of methylene chloride/diethyl ether=1/1. Yield 650 mg. M.p. 203°-5° C.

Workup

  1. customA solution prepared from 0.075 g
  2. additionwas added to a suspension of 0.640 g
  3. temperatureThe resulting mixture was refluxed for 30 minutes on an oil bath
  4. distillationthe ethanol was distilled off
  5. customat about 150° C
  6. customcrystallized out
  7. filtrationIt was recovered by filtration
  8. customre-crystallized from a mixture of methylene chloride/diethyl ether=1/1

Sources & evidence

ORD record
ord-5aa566769df0485e87dd5f72438d18fb
Source dataset
uspto-grants-1982_02
Patent number
US04313950

Reaction notes

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