Methyl iodide → HCID 20277052, compound

HRID 1248614Notes

Reaction equation

HRID 1248614 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:7][C:8]2([OH:17])[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[CH3:25]I.[I-]>C(O)C.O=[Pt]=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:7][C:8]2([OH:17])[CH:11]2[CH2:12][CH2:13][N:14]([CH3:25])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 30165Iodide IonHCID 20277050HCID 20277050, compound

Product 1

HCID 20277052HCID 20277052, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

6-Fluoro-3-(4'-fluorophenyl)-1-hydroxy-1-pyrid-4-ylindane (5.0 g) was reacted with methyliodide as described in Example 2, and the resulting pyridylium iodide (viscous oil) was dissolved in ethanol (150 ml) and 0.5 g PtO2 added. The estimated amount of hydrogen was consumed in 3 hrs. (3.0-3.5 atm.). The catalyst was filtered off and the ethanol evaporated. Ice-cold NaOH solution (100 ml 0.2M) was added to the residue and the resulting base extracted with ethyl acetate (2×50 ml). The combined organic phases were dried (MgSO4) and the solvent evaporated. The remaining oil was dissolved in isopropylether, and by cooling the product precipitated and was filtered off. Yield: 4.7 g (88.8%) of the title compound. MP: 146°-147° C.

Workup

  1. customThe estimated amount of hydrogen was consumed in 3 hrs
  2. filtrationThe catalyst was filtered off
  3. customthe ethanol evaporated
  4. additionIce-cold NaOH solution (100 ml 0.2M) was added to the residue
  5. extractionthe resulting base extracted with ethyl acetate (2×50 ml)
  6. dry with materialThe combined organic phases were dried (MgSO4)
  7. customthe solvent evaporated
  8. dissolutionThe remaining oil was dissolved in isopropylether
  9. temperatureby cooling the product
  10. customprecipitated
  11. filtrationwas filtered off

Sources & evidence

ORD record
ord-1b73a2a7dd9a4bcab05e71cf0bf59594
Source dataset
uspto-grants-1985_06
Patent number
US04525360

Reaction notes

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