Iodine → HCID 20335494, compound

HRID 1706444Notes

Reaction equation

HRID 1706444 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.[CH3:12][CH:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([CH3:25])[CH:19]=[CH:18]2)[CH3:14].[I:26]I.C1(C)C=CC=CC=1>C(OCC)(=O)C>[I-:26].[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N+:8]3[CH:25]=[C:20]4[CH:19]=[CH:18][C:17]5[CH:16]=[C:15]([CH:13]([CH3:14])[CH3:12])[CH:24]=[CH:23][C:22]=5[N:21]4[C:7]=3[CH:6]=[CH:5][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 1140TolueneHCID 196975Quinoline, 6-fluoro-HCID 13327718HCID 13327718, compound

Product 1

HCID 20335494HCID 20335494, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 88.3 g. of 6-fluoroquinoline, 27.8 g. of 6-(1-methylethyl)quinaldine and 76.2 g. of iodine in 100 ml. of toluene is heated at 95°-100° C. for 5 days, cooled and diluted with 350 ml. of ethyl acetate. The precipitate is collected, pulverized, suspended in 500 ml. of aqueous methanol and recovered by filtration. The solid is suspended in 400 ml. of cold methanol, stirred with 6 ml. of hydrazine and the solid 3-fluoro-10-(1-methylethyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration; m.p. 305°-307° C., after crystallization from methanol.

Workup

  1. temperaturecooled
  2. additiondiluted with 350 ml
  3. customThe precipitate is collected
  4. filtrationof aqueous methanol and recovered by filtration
  5. filtrationof hydrazine and the solid 3-fluoro-10-(1-methylethyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  6. customm.p. 305°-307° C., after crystallization from methanol

Sources & evidence

ORD record
ord-8dd2d370710b4368a67aa7ed569b2dbc
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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