Iodine → 3-Fluoroimidazo[1,2-a: 3,4-a']diquinolin-15-ium Iodide

HRID 1706442Notes

Reaction equation

HRID 1706442 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[N:12]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:13]=1[CH3:14].[I:23]I>ClC1C=CC=CC=1>[I-:23].[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N+:8]3[CH:14]=[C:13]4[CH:15]=[CH:16][C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=5[N:12]4[C:7]=3[CH:6]=[CH:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 70602-MethylquinolineHCID 196975Quinoline, 6-fluoro-

Product 1

HCID 203355523-Fluoroimidazo[1,2-a: 3,4-a']diquinolin-15-ium Iodide

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 294 g. of 6-fluoroquinoline, 74.6 g. of quinaldine, 1.7 l. of chlorobenzene and 254 g. of iodine is stirred for 2 hours at 20°-25° C., then stirred and heated at 100° C. for 4 days. About 1 l. of solvent is removed by evaporation at reduced pressure and the residue is cooled to 0°-5° C. The precipitate is collected, washed with cold chlorobenzene, dried and pulverized. The finely divided solid is suspended with stirring and cooling in 500 ml. of methanol and 55 ml. of hydrazine is added to destroy excess iodine. The resulting solid 3-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration, washed with cold methanol and dried; m.p. 310°-316° C.

Workup

  1. additionA mixture of 294 g
  2. customof solvent is removed by evaporation at reduced pressure
  3. temperaturethe residue is cooled to 0°-5° C
  4. customThe precipitate is collected
  5. washwashed with cold chlorobenzene
  6. customdried
  7. stirringwith stirring
  8. temperaturecooling in 500 ml
  9. additionof hydrazine is added
  10. customto destroy excess iodine
  11. filtrationThe resulting solid 3-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  12. washwashed with cold methanol
  13. customdried

Sources & evidence

ORD record
ord-a54365e190164eed8298e80765256138
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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