P-Anisidine → Ethyl 6-methoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate

HRID 1956429Notes

Reaction equation

HRID 1956429 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:13][O:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:2]2[NH:25][C:24]1[CH:26]=[CH:27][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 7732P-Anisidine2×HCID 11430Potassium Carbonate2×HCID 23209173Ethyl 4-chloro-6-methoxy-1,5-naphthyridine-3-carboxylate

Product 1

HCID 23209166Ethyl 6-methoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-chloro-6-methoxy-1,5-naphthyridine-3-carboxylate (1.68 g), 4-methoxyaniline (0.78 g), dry THF (50 ml) and anhydrous potassium carbonate (1.74 g) was stirred at ambient temperature for 7 hours. Further amounts of 4-methoxyaniline (0.4 g) and anhydrous potassium carbonate (0.9 g) were added and the mixture stirred at ambient temperature for 32 hours. The mixture was evaporated to dryness and the residue diluted with water (100 ml). The mixture was extracted into dichloromethane to give an oil which solidified. The solid was purified by column chromatography on silica using ethyl acetate as the mobile phase to give ethyl 6-methoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate, m.p. 115°-117° C.

Workup

  1. stirringthe mixture stirred at ambient temperature for 32 hours
  2. customThe mixture was evaporated to dryness
  3. additionthe residue diluted with water (100 ml)
  4. extractionThe mixture was extracted into dichloromethane
  5. customto give an oil which
  6. customThe solid was purified by column chromatography on silica

Sources & evidence

ORD record
ord-c6946770221947b9b3867228578e2fa6
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

Loading…