Ammonia → Ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate

HRID 1956415Notes

Reaction equation

HRID 1956415 reaction equation
[CH2:1]([O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]2O)[CH3:2].P(Cl)(Cl)([Cl:22])=O.N>>[Cl:22][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([O:3][CH2:1][CH3:2])[N:5]=2)[N:10]=[CH:9][C:8]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178469593HCID 178469593, compound

Product 1

HCID 23209292Ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate

Procedure

Ethyl 6-ethoxy-4-hydroxy-1,5-naphthyridine-3-carboxylate (3.0 g) was added to phosphorus oxychloride (25 ml), with stirring, at ambient temperature. The mixture was heated at 50° C. for 45 minutes. The mixture was cooled to 10° C. and added to ice/water at less than 5° C. The mixture was then basified with concentrated aqueous ammonia solution SG 0.88 at less than 5° C. The mixture was extracted with dichloromethane to give ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate, m.p. 61°-64° C.

Workup

  1. temperatureThe mixture was heated at 50° C. for 45 minutes
  2. temperatureThe mixture was cooled to 10° C.
  3. extractionThe mixture was extracted with dichloromethane

Sources & evidence

ORD record
ord-4532762708194e3180267e48e8780101
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

Loading…