Iodine → HCID 20335583, compound

HRID 1706448Notes

Reaction equation

HRID 1706448 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[F:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[CH:17]2.[I:24]I>ClC1C=CC=CC=1>[I-:24].[F:13][C:14]1[CH:23]=[CH:22][C:21]2[N+:20]3[CH:12]=[C:7]4[CH:6]=[CH:5][C:4]5[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:9]=5[N:8]4[C:19]=3[CH:18]=[CH:17][C:16]=2[CH:15]=1

Participants

5

Reactant 3

HCID 807IodineHCID 707846-Fluoro-2-methylquinolineHCID 196975Quinoline, 6-fluoro-

Product 1

HCID 20335583HCID 20335583, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 16.1 g. of 6-fluoroquinaldine, 58.9 g. of 6-fluoroquinoline, 70 ml. of chlorobenzene and 50.8 g. of iodine is stirred at 20°-25° C. for 1 hour, then heated at 95°-100° C. for 4 days. The precipitate is collected and suspended in 300 ml. of methanol. The methanol suspension is treated with 17 ml. of 85% hydrazine hydrate and the resulting solid 3,10-difluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration; m.p. >360° C., after crystallization from methanol.

Workup

  1. additionA mixture of 16.1 g
  2. temperatureheated at 95°-100° C. for 4 days
  3. customThe precipitate is collected
  4. additionThe methanol suspension is treated with 17 ml
  5. filtrationof 85% hydrazine hydrate and the resulting solid 3,10-difluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  6. customm.p. >360° C., after crystallization from methanol

Sources & evidence

ORD record
ord-1baaad0956bd468d943c1081cd94ebfe
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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