Iodine → HCID 19867068, compound

HRID 1904385Notes

Reaction equation

HRID 1904385 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]=[CH:9][N:10]([C:12]2[CH:13]=[C:14]3[C:19](=[C:20]([CH3:22])[CH:21]=2)[NH:18][C:17](=[O:23])[CH:16]=[CH:15]3)[CH:11]=1.[I:24]I.[Cl-].[NH4+]>CCCCCC.O1CCCC1.O>[I:24][C:9]1[N:10]([C:12]2[CH:13]=[C:14]3[C:19](=[C:20]([CH3:22])[CH:21]=2)[NH:18][C:17](=[O:23])[CH:16]=[CH:15]3)[CH:11]=[C:7]([CH3:6])[N:8]=1

Participants

8

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 14450301HCID 14450301, compoundHCID 178418339Butyllithium

Product 1

HCID 19867068HCID 19867068, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

n-Butyllithium (2.94 cm3 of a 1.43 M solution in n-hexane was added dropwise to a stirred suspension of 6-(4-methylimidazol1-yl)-8-methyl-2-(1H)-quinolone (0.45 g) (see Example 6) in tetrahydrofuran (THF) (25 cm3) at -70° C. under nitrogen. After one hour iodine (0.51 g) was added and the mixture warmed to room temperature over 1.5 hours. Ammonium chloride solution was added (5 cm3), and the mixture was poured into water (20 cm3). The aqueous mixture was extracted with dichloromethane (3×50 cm3) and the combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]). Elution with chloroform followed by combination and evaporation of appropriate fractions gave a solid which was recrystallised from ethyl acetate to afford 6-(2-iodo-4-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, m.p. (d) 260° (0.22 g).

Workup

  1. extractionThe aqueous mixture was extracted with dichloromethane (3×50 cm3)
  2. dry with materialdried (MgSO4) organic extracts
  3. customwere evaporated in vacuo
  4. customto give a residue which
  5. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  6. washElution with chloroform
  7. customfollowed by combination and evaporation of appropriate fractions
  8. customgave a solid which
  9. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-9ddac8d719e34b94a6505ee93543652c
Source dataset
uspto-grants-1989_06
Patent number
US04837334

Reaction notes

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