Triethylamine → HCID 19010529, compound

HRID 1741730Notes

Reaction equation

HRID 1741730 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH3:15])=[N+:12]([O-])[CH:13]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:18].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:15][Cl:18])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychloride2×HCID 516892Sodium BicarbonateHCID 19010536HCID 19010536, compound

Product 1

HCID 19010529HCID 19010529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 5-(4-fluorophenyl)-2-methylpyridine-N-oxide (2.9 g, 14.5 mmol) in CH2Cl2 (15 mL) is added a 1.5 mL portion of a CH2Cl2 (15 mL) solution of POCl3 (1.72 g, 1.7 mmol). Subsequently, the remainder of this POCl3 solution and a solution of triethylamine (1.76 g, 17.4 mmol) in CH2Cl2 (15 mL) are added simultaneously, so as to maintain reflux. After addition is complete the resulting solution is stirred at ambient temperature for 2 hours. The reaction mixture is then neutralized by addition of saturated NaHCO3 (50 mL). The organic phase is separated, dried over MgSO4 and concentrated in vacuo. Chromatography (silica gel, 1:1 EtOAc/hexanes) affords 5-(4-fluorophenyl)-2-(chloromethyl)pyridine as a yellow solid.

Workup

  1. temperatureso as to maintain
  2. temperaturereflux
  3. additionAfter addition
  4. customThe organic phase is separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36b65f5fb83c45108601065fb0dedac2
Source dataset
uspto-grants-1994_08
Patent number
US05334600

Reaction notes

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