Ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylate → Ethyl 7-methyl-4-[4-(2-pyridyloxy)anilino]-1,8-naphthyridine-3-carboxylate hydrochloride

HRID 1956453Notes

Reaction equation

HRID 1956453 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1>>[ClH:1].[CH3:12][C:8]1[N:7]=[C:6]2[C:11]([C:2]([NH:29][C:28]3[CH:27]=[CH:26][C:25]([O:24][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=4)=[CH:31][CH:30]=3)=[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 10562672Ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylateHCID 131505744-(Pyridin-2-yloxy)aniline

Product 1

HCID 23209214Ethyl 7-methyl-4-[4-(2-pyridyloxy)anilino]-1,8-naphthyridine-3-carboxylate hydrochloride

Procedure

A mixture of ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylate (2.49 g) and 4-(2-pyridyloxy)aniline (1.85 g) in IMS (50 ml) was boiled under reflux for 1 hour. The mixture was allowed to stand at ambient temperature overnight and then evaporated under reduced pressure. The residue was triturated with ethyl acetate and filtered to give a solid which was recrystallised from ethanol/ethyl acetate. This solid was dissolved in IMS and hydrogen chloride gas was bubbled through the solution with cooling. The solvent was then evaporated under reduced pressure and the residue was recrystallised from ethanol/ethyl acetate to give ethyl 7-methyl-4-[4-(2-pyridyloxy)anilino]-1,8-naphthyridine-3-carboxylate hydrochloride, m.p. 207°-208° C. Active (2/2) at 30 mg/kg.

Workup

  1. temperatureunder reflux for 1 hour
  2. customevaporated under reduced pressure
  3. customThe residue was triturated with ethyl acetate
  4. filtrationfiltered
  5. customto give a solid which
  6. customwas recrystallised from ethanol/ethyl acetate
  7. dissolutionThis solid was dissolved in IMS
  8. customhydrogen chloride gas was bubbled through the solution
  9. temperaturewith cooling
  10. customThe solvent was then evaporated under reduced pressure
  11. customthe residue was recrystallised from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-acb18dec1a764981bffcbad52d715088
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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