Phosphorus oxychloride → (E)-3-[2-Chloro-5-(4-fluorophenyl)-7-isopropyl-1,8-naphthyridin-6-yl]-prop-2-enal

HRID 1087050Notes

Reaction equation

HRID 1087050 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](/[CH:18]=[CH:19]/[CH:20]=[O:21])=[C:16]([CH:22]([CH3:24])[CH3:23])[N:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12](=O)[NH:13]3)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:12]1[CH:11]=[CH:10][C:9]2[C:14](=[N:15][C:16]([CH:22]([CH3:24])[CH3:23])=[C:17](/[CH:18]=[CH:19]/[CH:20]=[O:21])[C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14850559(E)-3-[5-(4-Fluorophenyl)-1,2-dihydro-7-isopropyl-2-oxo1, 8-naphthyridin-6-yl]-prop-2-enal

Product 1

HCID 19817640(E)-3-[2-Chloro-5-(4-fluorophenyl)-7-isopropyl-1,8-naphthyridin-6-yl]-prop-2-enal

Procedure

7.8 g (23 mmol) of the compound from Example 5 are heated to 75° C. in 20 ml of phosphorus oxychloride. After a clear solution has formed, the mixture is concentrated in vacuo, the residue is dissolved in ethyl acetate, and the solution is poured into ice water and stirred vigorously. The aqueous phase is extracted twice with ethyl acetate, the combined organic phases are dried and the solvent is stripped off. 5.78 g (71%) of colorless crystals of m.p.: 142° C. crystallize from ether.

Workup

  1. customAfter a clear solution has formed
  2. concentrationthe mixture is concentrated in vacuo
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. additionthe solution is poured into ice water
  5. extractionThe aqueous phase is extracted twice with ethyl acetate
  6. customthe combined organic phases are dried
  7. custom5.78 g (71%) of colorless crystals of m.p.: 142° C. crystallize from ether

Sources & evidence

ORD record
ord-21dae1f0e04c45be8932cfe3d30ba98c
Source dataset
uspto-grants-1991_07
Patent number
US05034399

Reaction notes

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