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

HRID 1956429ノート

反応式

HRID 1956429 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c6946770221947b9b3867228578e2fa6
出典データセット
uspto-grants-1998_07
特許番号
US05780482

反応ノート

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