Acetic Acid → HCID 68527178, compound

HRID 1932483Notes

Reaction equation

HRID 1932483 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20]CC(OCC)=O)=[CH:16][CH:15]=2)=[N:11][CH:12]=1.C=O.[C:33]([OH:36])(=[O:35])[CH3:34].[C:37]([BH3-])#N.[Na+].[OH-].[Na+].Cl>C(O)C.O>[Cl:30][C:29]1[CH:28]=[C:27]([CH:37]=[CH:3][C:2]=1[Cl:1])[CH2:4][CH2:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH2:34][C:33]([OH:36])=[O:35])=[CH:18][CH:19]=2)=[N:11][CH:12]=1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 68524328HCID 68524328, compound

Product 1

HCID 68527178HCID 68527178, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-{4-[5-(3,4-dichlorobenzylamino)pyridin-2-yloxy]phenyl}propionate (1.63 g, 3.7 mmol) in ethanol (30 mL) were added 37% aqueous formaldehyde (2.0 mL, 22 mmol) and acetic acid (0.21 mL, 3.7 mmol), and the resulting solution was stirred at room temperature for 1 hour. To this solution was then added sodium cyanoborohydride (0.46 g, 7.3 mmol) at 0° C., and the resulting solution was stirred at the same temperature for 1 hour. To this solution was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), to thereby yield 1.55 g of ethyl 3-{4-[5-(3,4-dichlorobenzylmethylamino)-pyridin-2-yloxy]phenyl}propionate. This product was dissolved in ethanol (40 mL), and to the resulting solution was added 10% aqueous sodium hydroxide (2.7 mL, 6.7 mmol) and stirred at room temperature for 2 hours. The resulting solution was then acidified by adding 10% hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated, to thereby yield 1.44 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)
  6. dissolutionThis product was dissolved in ethanol (40 mL)
  7. stirringstirred at room temperature for 2 hours
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-d3c257c9f1d44b5d9d1a7e600b3c7802
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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