Iodine → HCID 20335504, compound

HRID 1706445Notes

Reaction equation

HRID 1706445 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH3:22])[CH:16]=[CH:15]2.[I:23]I>ClC1C=CC=CC=1>[I-:23].[F:11][C:12]1[CH:21]=[CH:20][C:19]2[N:18]3[C:2]4[CH:3]=[CH:4][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=5[N+:1]=4[CH:22]=[C:17]3[CH:16]=[CH:15][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 807IodineHCID 7047QuinolineHCID 707846-Fluoro-2-methylquinoline

Product 1

HCID 20335504HCID 20335504, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 614 g. of quinoline, 192 g. of 6-fluoroquinaldine [J. Org. Chem. 42, 911 (1977)], 2.0 l. of chlorobenzene and 602 g. of iodine is stirred at 25°-30° C. for 2 hours, then heated at 95°-100° C. for 90 hours. The mixture is cooled and the precipitate is collected, washed with cold chlorobenzene and suspended in 1.5 l. of methanol. The methanol suspension is stirred with 150 ml. of hydrazine hydrate and the resulting solid 10-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration; m.p. 330°-334° C., after crystallization from methanol.

Workup

  1. additionA mixture of 614 g
  2. temperatureheated at 95°-100° C. for 90 hours
  3. temperatureThe mixture is cooled
  4. customthe precipitate is collected
  5. washwashed with cold chlorobenzene
  6. filtrationof hydrazine hydrate and the resulting solid 10-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  7. customm.p. 330°-334° C., after crystallization from methanol

Sources & evidence

ORD record
ord-f8b89539ee3841da913978323692a237
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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