2-Chloronicotinoyl chloride → HCID 118492328, compound

HRID 710601Notes

Reaction equation

HRID 710601 reaction equation
C(O[C:4](=[C:9]=[O:10])[CH2:5][C:6]([OH:8])=[O:7])C.[CH2:11]([Li])[CH2:12]CC.[Cl:16][C:17]1[N:25]=[CH:24][CH:23]=[CH:22][C:18]=1C(Cl)=O>O1CCCC1>[CH2:11]([O:8][C:6](=[O:7])[CH2:5][C:4]([C:18]1[C:17]([Cl:16])=[N:25][CH:24]=[CH:23][CH:22]=1)=[C:9]=[O:10])[CH3:12]

Participants

5

Reactant 3

HCID 27745412-Chloronicotinoyl chlorideHCID 118492320HCID 118492320, compoundHCID 178418339Butyllithium

Product 1

HCID 118492328HCID 118492328, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-ethoxy-3-carbonylpropionic acid (13.2 g, 100 mmol) was dissolved in tetrahydrofuran (100 mL), n-butyl lithium (25.6 g, 400 mmol) was added dropwise at −78° C., reacted at low temperature for 1 h, 2-chloronicotinoyl chloride (17.5 g, 99.4 mmol) in tetrahydrofuran (20 mL) solution was added, and continuously reacted at low temperature for 3 h. After reaction was complete, extraction was performed with water/dichloromethane, organic phase was rotated for dryness, and separated by column chromatography to obtain product 13.8 g.

Workup

  1. customreacted at low temperature for 1 h
  2. customcontinuously reacted at low temperature for 3 h
  3. customAfter reaction
  4. extractionextraction
  5. customseparated by column chromatography

Sources & evidence

ORD record
ord-59e11d1444da4ec3a7bdb751cca23c62
Source dataset
uspto-grants-2015_11
Patent number
US09181244B1

Reaction notes

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