Hydrochloric Acid → HCID 57448040, compound

HRID 1879016Notes

Reaction equation

HRID 1879016 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, cone) 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-29f3d564e83f49b583fd8ff32a284566
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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