Thionyl Chloride → HCID 23151222, compound

HRID 2386973Notes

Reaction equation

HRID 2386973 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C([O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][C:24]=1[NH2:29])C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([NH:29][C:24]1[N:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([OH:30])=[O:21])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 5622014-(Benzyloxy)butanoic acidHCID 12433260Ethyl 2-aminopyridine-3-carboxylate

Product 1

HCID 23151222HCID 23151222, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

4-(benzyloxy)butyric acid (154 mg, 0.79 mmol) was dissolved in chloroform, thionyl chloride (158 mg) was added, and the mixture stirred at room temperature for 1 Hour. The solvent and excess thionyl chloride were distilled off under reduced pressure, the residue was dissolved in chloroform, triethylamine (0.46 mL) and 2-aminonicotinic acid ethyl ester (110 mg, 0.66 mmol) were added, and the mixture stirred at room temperature for 2 hours. Saturated sodium hydrogen carbonate aqueous solution was added to the reaction liquid, the mixture extracted with chloroform, and dried with anhydrous sodium sulfate. The obtained residue was dissolved in methanol, 2N sodium hydroxide aqueous solution (0.66 mL) was added, and the mixture stirred at room temperature for 2 hours. After adding hydrochloric acid aqueous solution to the reaction liquid to render it weakly acid, the solvent was distilled off under reduced pressure. Ethyl acetate and a small amount of ethanol were added to the residue, the solid precipitate was filtered off, and the target compound (166 mg, 80%) was thus obtained as a colorless solid.

Workup

  1. distillationThe solvent and excess thionyl chloride were distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. stirringthe mixture stirred at room temperature for 2 hours
  4. extractionthe mixture extracted with chloroform
  5. dry with materialdried with anhydrous sodium sulfate
  6. dissolutionThe obtained residue was dissolved in methanol
  7. addition2N sodium hydroxide aqueous solution (0.66 mL) was added
  8. stirringthe mixture stirred at room temperature for 2 hours
  9. additionAfter adding hydrochloric acid aqueous solution
  10. customto the reaction liquid
  11. distillationthe solvent was distilled off under reduced pressure
  12. additionEthyl acetate and a small amount of ethanol were added to the residue
  13. filtrationthe solid precipitate was filtered off

Sources & evidence

ORD record
ord-935b089d2b4d41ad9c81480079c650e6
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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