Iodine → HCID 20335477, compound

HRID 1706447Notes

Reaction equation

HRID 1706447 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[C:23]([CH3:28])[CH:22]=[CH:21]2.[I:29]I.O.NN>ClC1C=CC=CC=1.C1(C)C=CC=CC=1>[I-:29].[CH:1]1([C:7]2[CH:16]=[CH:15][C:14]3[N+:13]4[CH:28]=[C:23]5[CH:22]=[CH:21][C:20]6[CH:19]=[C:18]([F:17])[CH:27]=[CH:26][C:25]=6[N:24]5[C:12]=4[CH:11]=[CH:10][C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 807IodineHCID 24654Hydrazine hydrate (1:1)HCID 707846-Fluoro-2-methylquinolineHCID 20335626HCID 20335626, compound

Product 1

HCID 20335477HCID 20335477, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 85.0 g. of 6-cyclohexylquinoline, 16.4 g. of 6-fluoroquinaldine, 150 ml. of toluene and 51.6 g. of iodine is stirred for 30 minutes at 20-25° C., then heated at 95°-100° C. for 6 days. The mixture is cooled, diluted with 300 ml. of chlorobenzene and treated dropwise with hydrazine hydrate until the dark-colored mixture becomes light tan. The precipitate is collected, washed with chlorobenzene and suspended in 400 ml. of cold methanol. The resulting solid 3-cyclohexyl-10-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration and crystallized from dimethylformamide/methanol; m.p. ca 225° C.-235° C.

Workup

  1. additionA mixture of 85.0 g
  2. temperatureheated at 95°-100° C. for 6 days
  3. temperatureThe mixture is cooled
  4. additiondiluted with 300 ml
  5. customThe precipitate is collected
  6. washwashed with chlorobenzene
  7. filtrationThe resulting solid 3-cyclohexyl-10-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  8. customcrystallized from dimethylformamide/methanol

Sources & evidence

ORD record
ord-90dcc776dbd8412382597dcb60124c7a
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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