Hydrochloric Acid → HCID 22036022, compound

HRID 1789924Notes

Reaction equation

HRID 1789924 reaction equation
[C:1]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[N:10][CH:11]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].C(O)C.Cl>>[OH:5][CH:1]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[N:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 22036090HCID 22036090, compound

Product 1

HCID 22036022HCID 22036022, compoundYield 41.2%

Procedure

To a solution of N-(5-butyryl-pyridin-2-yl)-2,2-dimethyl-propionamide (2.47 g, 9.95 mmol) in ethanol (20 mL) sodium borohydride (185 mg, 5.0 mmol) was added. After 40 min stirring at room temperature the mixture was acidified with 1 N hydrochloric acid to pH 2 and stirred for 10 min. After neutralisation with sodium hydrogencarbonate the mixture was extracted three times with dichloromethane. The combined organic extracts were washed twice with sodium hydrogen carbonate solution and once with brine. After drying and concentration under reduced pressure the residue was purified by flash chromatography (dichloromethane/methanol 30:1) to give N-[5-(1-hydroxy-butyl)-pyridin-2-yl]-2,2-dimethyl-propionamide (1.025 g, 41%).

Workup

  1. stirringstirred for 10 min
  2. extractionAfter neutralisation with sodium hydrogencarbonate the mixture was extracted three times with dichloromethane
  3. washThe combined organic extracts were washed twice with sodium hydrogen carbonate solution and once with brine
  4. customAfter drying
  5. concentrationconcentration under reduced pressure the residue
  6. customwas purified by flash chromatography (dichloromethane/methanol 30:1)

Sources & evidence

ORD record
ord-8bbed489c50749129939c6d97a7a2daf
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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