Chlorosuccinimide → 4-Chloro-2-methoxypyridine

HRID 243758Notes

Reaction equation

HRID 243758 reaction equation
C([Mg][Cl:5])(C)C.I[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13][CH3:14])[CH:8]=1.COC1C=C([Mg]Cl)C=CN=1.ClN1C(=O)CCC1=O>O1CCCC1.O>[Cl:5][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13][CH3:14])[CH:8]=1

Participants

7

Reactant 4

HCID 31398ChlorosuccinimideHCID 150197954-Iodo-2-methoxypyridineHCID 178418918HCID 178418918, compoundHCID 178492981HCID 178492981, compound

Product 1

HCID 226385104-Chloro-2-methoxypyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

50.6 ml (2 mol/l tetrahydrofuran solution) of isopropylmagnesium chloride was cooled with ice, and a solution having 19.8 g (84.3 mmol) of crude 4-iodo-2-methoxypyridine obtained in Step (c) dissolved in 80 ml of tetrahydrofuran was added, followed by stirring at 0° C. for 1 hour and then at room temperature for 1 hour to prepare 2-methoxy-4-pyridylmagnesium chloride. Then, 16.9 g (127 mmol) of N-chlorosuccinimide was gradually added, followed by stirring at room temperature for 1 hour. 100 ml of water was added to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. After extraction with ethyl ether, the organic layer was dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 11.0 g (crude yield: 91%) of crude 4-chloro-2-methoxypyridine.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 1 hour
  3. customto terminate
  4. customthe reaction, and tetrahydrofuran
  5. distillationwas distilled off under reduced pressure
  6. extractionAfter extraction with ethyl ether
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. filtrationsubjected to filtration
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-175a2d8d66284e0ea4d7d35f60774473
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

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