Phosphorus oxychloride → HCID 14153005, compound

HRID 1194547Notes

Reaction equation

HRID 1194547 reaction equation
O[C:2]1[C:11]2[CH2:10][CH:9]([CH2:12][CH3:13])[CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:2]1[C:11]2[CH2:10][CH:9]([CH2:12][CH3:13])[CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469463HCID 178469463, compound

Product 1

HCID 14153005HCID 14153005, compound

Procedure

A solution of 3.5 g of ethyl 4-hydroxy-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate in 35 ml phosphorus oxychloride is heated to reflux under nitrogen for five hours. The POCl3 is removed under vacuum, the residue is dissolved in CHCl3, and the solution is washed with cold 2N NaOH, saturated NaCl, then dried over anhydrous MgSO4, and evaporated to dryness. The crude product is purified through a short column of silica gel eluting with EtOAc. Removal of solvent under vacuum affords ethyl 4-chloro-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate as an oil, which is used directly in the next step.

Workup

  1. temperatureto reflux under nitrogen for five hours
  2. customThe POCl3 is removed under vacuum
  3. dissolutionthe residue is dissolved in CHCl3
  4. washthe solution is washed with cold 2N NaOH, saturated NaCl
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated to dryness
  7. customThe crude product is purified through a short column of silica gel eluting with EtOAc
  8. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-b5f15c84388b4700954e66bd9fe94886
Source dataset
uspto-grants-1989_03
Patent number
US04814450

Reaction notes

Loading…