Hydrochloric Acid → HCID 57448040, compound

HRID 2358106Notes

Reaction equation

HRID 2358106 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.Cl>CO.C(=O)([O-])[O-].[Na+].[Na+].[Pt]=O>[CH3:1][O:2][C:3]1[C:8]([C:9]([F:10])([F:12])[F:11])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 46317318HCID 46317318, compound

Product 1

HCID 57448040HCID 57448040, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 4-[2-methoxy-3-(trifluoro-methyl)phenyl]pyridine (0.42 g, 1.66 mmol) in methanol (10 ml), was added platinum oxide (0.10 g) and hydrochloric acid (0.1 ml, conc) and the reaction mixture was hydrogenated at 50 psi for 1 h under hydrogen. Filtration through a pad of celite and evaporation of the filtrate gave 0.48 g of crude product as the hydrochloric acid salt. The salt was dissolved in aqueous sodium carbonate (10%, 50 ml) and extracted with ethylacetate (3×50 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness to give the title compound (0.38 g). MS m/z (relative intensity, 70 eV) 260 (M+, 2), 258 (M+, 7), 229 (14), 228 (bp) 59 (15).

Workup

  1. filtrationFiltration
  2. customthrough a pad of celite and evaporation of the filtrate
  3. customgave 0.48 g of crude product as the hydrochloric acid salt
  4. extractionextracted with ethylacetate (3×50 ml)
  5. dry with materialThe combined organic phases was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-b24a0761f7dc418298949b44ff8bddf0
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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