Potassium Carbonate → HCID 23209287, compound

HRID 1956431Notes

Reaction equation

HRID 1956431 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].[OH:20][CH2:21][CH2:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>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:28][C:27]1[CH:26]=[CH:25][C:24]([O:23][CH2:22][CH2:21][OH:20])=[CH:30][CH:29]=1)[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 808922-(4-Aminophenoxy)ethanolHCID 23209292Ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate

Product 1

HCID 23209287HCID 23209287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate (2.4 g), 4-(2-hydroxyethoxy)aniline (1.4 g), anhydrous potassium carbonate (2.49 g) and THF (70 ml) was stirred at ambient temperature for 3 days. The mixture was filtered and the filtrate evaporated to dryness. The residue was ground up in ether and filtered. The residue was dissolved in dichloromethane and purified by chromatography on silica. The product fractions were combined, dissolved in IMS (150 ml) and saturated with hydrogen chloride gas. The mixture was cooled in ice and diluted with ether to induce precipitation. The mixture was filtered to give ethyl 6-ethoxy-4-[4-(2-hydroxyethoxy)anilino]-1,5-naphthyridine-3-carboxylate hydrochloride, m.p. 177°-178° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. filtrationfiltered
  4. dissolutionThe residue was dissolved in dichloromethane
  5. custompurified by chromatography on silica
  6. dissolutiondissolved in IMS (150 ml) and saturated with hydrogen chloride gas
  7. temperatureThe mixture was cooled in ice
  8. additiondiluted with ether
  9. customprecipitation
  10. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-90ea3354755848e284ee6fd8800a1aa8
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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