Iodide Ion → HCID 10427137, compound

HRID 275358Notes

Reaction equation

HRID 275358 reaction equation
[CH3:1][C:2]1[N:3]([C:19]2[CH:24]=[CH:23][N+:22]([CH3:25])=[CH:21][CH:20]=2)[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[CH:8][C:7]([CH3:18])=[CH:6][CH:5]=2.[I-]>C(O)(=O)C.O=[Pt]=O>[CH3:1][C:2]1[N:3]([CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:4]2[C:9]([C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)=[CH:8][C:7]([CH3:18])=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 30165Iodide IonHCID 10027159HCID 10027159, compound

Product 1

HCID 10427137HCID 10427137, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

4-[2,5-Dimethyl-3-(4-fluorophenyl)-1H-indol-1-yl]-1-methylpyridinium, iodide 8a (3.0 g) was dissolved in acetic acid (75 ml) and PtO2 (0.4 g) was added. After hydrogenation for 2 weeks at 3 ato the catalyst was filtered off, the acetic acid was evaporated in vacuo and water (50 ml) was added. The thus obtained acidic solution was made alkaline (pH>9) with concentrated sodium hydroxide and extracted with ethyl acetate (2×50 ml). The organic phases were successively washed with diluted sodium hydroxide (50 ml), washed with brine and dried (Na2SO4). Evaporation of the solvent gave 1.3 g of the title compound as an oil, which was purified by column chromatography on silica gel (eluted with ethyl acetate/ethanol 8:1 containing 4% triethylamine) and crystallized from heptane. Yield 0.4 g, mp 110°-112° C.

Workup

  1. filtrationAfter hydrogenation for 2 weeks at 3 ato the catalyst was filtered off
  2. customthe acetic acid was evaporated in vacuo and water (50 ml)
  3. additionwas added
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe organic phases were successively washed with diluted sodium hydroxide (50 ml)
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-536c9d69f110484e9bb99d8e8623613b
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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