Phosphorus oxychloride → HCID 86664336, compound

HRID 1753901Notes

Reaction equation

HRID 1753901 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][C:9](=O)[NH:8][C:7]=1[CH:16]([CH3:18])[CH3:17])=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:21]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH:16]([CH3:18])[CH3:17])=[N:8][C:9]([Cl:21])=[CH:10][C:11]=1[CH:12]([CH3:14])[CH3:13])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67286838HCID 67286838, compound

Product 1

HCID 86664336HCID 86664336, compoundYield 85%

Procedure

A solution of 2.2 g (8.76 mmol) 2,4-diisopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethylester in POCl3 (43.8 ml) was stirred at 120° C. for 2 h. Then excess POCl3 was evaporated. The residue was dissolved in EtOAc (60 ml) and the solution was washed with a sat. NaHCO3 sol, water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. Purification of this residue by CC (hexane/EtOAc 97:3) provided 2.0 g (7.43 mmol, 85%) 6-chloro-2,4-diisopropyl-pyridine-3-carboxylic acid ethylester.

Workup

  1. customThen excess POCl3 was evaporated
  2. dissolutionThe residue was dissolved in EtOAc (60 ml)
  3. washthe solution was washed with a sat. NaHCO3 sol, water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification of this residue by CC (hexane/EtOAc 97:3)

Sources & evidence

ORD record
ord-88be26e8958a4c209b55afe58783ee54
Source dataset
uspto-grants-2015_10
Patent number
US09168259B2

Reaction notes

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