Hydrochloric Acid → Ethyl 6-ethoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate hydrochloride

HRID 1956428Notes

Reaction equation

HRID 1956428 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH3:14])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:20][O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CCOCC.C1COCC1>[ClH:1].[CH2:13]([O:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:2]2[NH:26][C:25]1[CH:27]=[CH:28][C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 23209292Ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate

Product 1

HCID 23209239Ethyl 6-ethoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate (17.95 g), 4-methoxyaniline (8.29 g), anhydrous potassium carbonate (18.6 g) and THF (250 ml) was stirred at ambient temperature for 48 hours. The mixture was evaporated to dryness and water was added to the residue. The mixture was extracted with dichloromethane to give a solid which was dissolved in IMS (50 ml). The solution was saturated with hydrogen chloride gas whilst cooling the mixture in ice. Ether was added to induce precipitation. The solid was collected by filtration to give ethyl 6-ethoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate hydrochloride, m.p. 160°-162° C. Active (3/3) at 30 mg/kg.

Workup

  1. customThe mixture was evaporated to dryness and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with dichloromethane
  4. customto give a solid which
  5. temperaturewhilst cooling the mixture in ice
  6. customprecipitation
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-50d50856ef984b19b557cf42adbf2a90
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

Loading…