Hydrochloric Acid → HCID 23209185, compound

HRID 1956427Notes

Reaction equation

HRID 1956427 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.Cl>CCOCC>[OH2:12].[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

5

Reactant 3

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

Product 1

HCID 23209185HCID 23209185, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl 4-chloro-6-ethoxy-1,5-naphthyridine-3-carboxylate (3.1 g), 4-methoxyaniline (1.36 g) and IMS (40 ml) was boiled under reflux for 4 hours. The mixture was evaporated to dryness. The residual solid was ground in ether and then filtered. The solid was dissolved in dichloromethane and purified by column chromatography on silica using dichloromethane, then ether, then ethyl acetate, then IMS, as the mobile phase. The third fraction obtained was dissolved in IMS (30 ml) and the solution was saturated with hydrogen chloride gas. Ether was added and the mixture left to stand at approximately 4° C. for 3 days. The mixture was filtered to give ethyl 6-ethoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate hydrochloride hydrate, m.p. 130°-133° C. Active (3/3) at 30 mg/kg.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe mixture was evaporated to dryness
  3. filtrationfiltered
  4. dissolutionThe solid was dissolved in dichloromethane
  5. custompurified by column chromatography on silica
  6. customThe third fraction obtained
  7. waitthe mixture left
  8. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-044b6614de1b40e08e71002b3fdd0718
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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