Phosphorus oxychloride → HCID 86720177, compound

HRID 1770663Notes

Reaction equation

O[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([CH3:17])[C:9]2[C:4](=[CH:5][C:6]([C:18]([F:21])([F:20])[F:19])=[CH:7][N:8]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([CH3:17])[C:9]2[C:4](=[CH:5][C:6]([C:18]([F:21])([F:20])[F:19])=[CH:7][N:8]=2)[N:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178470058HCID 178470058, compound

Product 1

HCID 86720177HCID 86720177, compoundYield 88%

Conditions

Temperature: 110 °C

Procedure

To ethyl 2-hydroxy-4-methyl-7-(trifluoromethyl)-1,5-naphthyridine-3-carboxylate (1.05 g, 3.50 mmol, 1 eq.) was added POCl3 (11 ml) at RT and the reaction mixture was heated to reflux at 110° C. for 3 h. Afterwards excess POCl3 was distilled off and the residue was diluted with EtOAc (50 ml). The mixture was washed with a sat. solution of NaHCO3 (50 ml), water (50 ml), brine (50 ml), dried over anhydrous Na2SO4 and evaporated to provide ethyl 2-chloro-4-methyl-7-(trifluoromethyl)-1,5-naphthyridine-3-carboxylate (0.98 g, 3.08 mmol, 88%), which was used in subsequent reactions without further purification.

Workup

temperaturethe reaction mixture was heated
distillationAfterwards excess POCl3 was distilled off
additionthe residue was diluted with EtOAc (50 ml)
washThe mixture was washed with a sat. solution of NaHCO3 (50 ml), water (50 ml), brine (50 ml)
dry with materialdried over anhydrous Na2SO4
customevaporated

Sources & evidence

ORD record: ord-133f1d0b707546d394c45225d46d6249
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248122B2

Reaction notes

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