Hydrochloric Acid → HCID 17958609, compound

HRID 2243283Notes

Reaction equation

HRID 2243283 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H-].[Na+].[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>CN(C=O)C.O.C(OCC)(=O)C>[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 615235-Phenyl-1-pentanolHCID 762582-Chloronicotinic acid

Product 1

HCID 17958609HCID 17958609, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 1.00 g (6.35 mmol) of 2-chloronicotinic acid is slowly added to a suspension of 635 mg (15.9 mmol) of 60% sodium hydride in 25 ml of DMF, and the mixture is then stirred at 0° C. for 30 min. 1.15 g (6.98 mmol) of 5-phenyl-1-pentanol are dissolved in 5 ml of DMF and slowly added dropwise to the above reaction solution. The solution is stirred at room temperature for 3.5 hours. It is then heated at 75° C. and stirred overnight. The substance is taken up in water, ethyl acetate is then added and the aqueous phase is acidified using 1M HCl. The mixture is then extracted with ethyl acetate and the extract is washed with water, dried over magnesium sulfate and concentrated under reduced pressure.

Workup

  1. additionslowly added dropwise to the above reaction solution
  2. stirringThe solution is stirred at room temperature for 3.5 hours
  3. temperatureIt is then heated at 75° C.
  4. stirringstirred overnight
  5. extractionThe mixture is then extracted with ethyl acetate
  6. washthe extract is washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac5ae4f053c14b9ea4f283e5dc137aeb
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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