2-Chloropyridine → HCID 19854561, compound

HRID 1649721Notes

Reaction equation

HRID 1649721 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10].[CH2:18]([Mg]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[CH2:18]([CH:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 79772-ChloropyridineHCID 15891Phenyl chloroformateHCID 178418336HCID 178418336, compound

Product 1

HCID 19854561HCID 19854561, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4 chloropyridine (2.50 g) in tetrahydrofuran is chilled to 40° . Phenyl chloroformate (2.8 ml) is then added dropwise, and the resulting thick slurry is warmed to -20° . A solution of 1M benzylmagnesium chloride in tetrahydrofuran (22 ml) is added dropwise, taking care to maintain the temperature below 0°. Upon completion of the addition, the cooling bath is removed and the reaction allowed to warm to room temperature. The reaction is then treated with 50% saturated aqueous ammonium chloride and diluted with diethyl ether (200 ml). The organic phase is washed with 1N hydrochloric acid (50 ml) and 1M disodium hydrogen phosphate (50 ml). Drying and concentration of the organic phase affords the intermediate 2-benzyl-1-carbophenoxy-1,2-dihydropyridine as an oil (7.2 g).

Workup

  1. temperaturethe resulting thick slurry is warmed to -20°
  2. temperatureto maintain the temperature below 0°
  3. additionUpon completion of the addition
  4. customthe cooling bath is removed
  5. additionThe reaction is then treated with 50% saturated aqueous ammonium chloride
  6. additiondiluted with diethyl ether (200 ml)
  7. washThe organic phase is washed with 1N hydrochloric acid (50 ml) and 1M disodium hydrogen phosphate (50 ml)
  8. customDrying

Sources & evidence

ORD record
ord-b1c63db96476464f86b76394089c5abc
Source dataset
uspto-grants-1990_05
Patent number
US04921857

Reaction notes

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