HCID 11244270, compound → HCID 9851847, compound

HRID 1723475Notes

Reaction equation

HRID 1723475 reaction equation
[Br-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N+:12]([CH3:15])=[CH:11][C:10]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:5][CH:4]=1>C(O)C.[Pt]=O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][C@H:10]2[C:16]([O:18][CH3:19])=[O:17])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 11244270HCID 11244270, compound

Product 1

HCID 9851847HCID 9851847, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

4-(4'-Fluorophenyl)-3-methoxycarbonyl-1-methylpyridinium bromide (15.90 g), prepared as in Example 1, in ethanol (250 ml) was hydrogenated at atmospheric pressure and 45° for 24 hours, in the presence of platinum oxide (0.5 g). Evaporation of the filtrate after removing the catalyst gave a dark oil which was partitioned between 10% sodium carbonate solution (100 ml) and dichloromethane (30 ml). After separation, the aqueous phase was extracted with dichloromethane (3×20 ml) and the organic solutions dried (potassium carbonate) and evaporated to give an off-white solid (12.1 g). Crystallisation from ethyl acetate gave the title compound as white crystals (8.32 g, 72%), m.p. 88°-89°.

Workup

  1. customEvaporation of the filtrate
  2. customafter removing the catalyst
  3. customgave a dark oil which
  4. customwas partitioned between 10% sodium carbonate solution (100 ml) and dichloromethane (30 ml)
  5. customAfter separation
  6. extractionthe aqueous phase was extracted with dichloromethane (3×20 ml)
  7. dry with materialthe organic solutions dried (potassium carbonate)
  8. customevaporated

Sources & evidence

ORD record
ord-6d9cb9680a45440a8f22afdfb477697d
Source dataset
uspto-grants-1989_08
Patent number
US04861893

Reaction notes

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