Phosphoric Acid → 4-(3-bromophenyl)-1,7-diethyl-5-methyl-1,8-naphthyridin-2(1H)-one

HRID 398835

反応式

HRID 398835 の反応式
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(=O)(O)(O)O.[NH2:20][C:21]1[N:26]([CH2:27][CH3:28])[C:25](=[O:29])[CH:24]=[C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([Br:36])[CH:31]=2)[CH:22]=1.[CH3:37][C:38](=O)[CH2:39][C:40](=O)[CH2:41][CH3:42].[OH-].[Na+]>>[Br:36][C:32]1[CH:31]=[C:30]([C:23]2[C:22]3[C:21](=[N:20][C:40]([CH2:41][CH3:42])=[CH:39][C:38]=3[CH3:37])[N:26]([CH2:27][CH3:28])[C:25](=[O:29])[CH:24]=2)[CH:35]=[CH:34][CH:33]=1

参加物

6

反応物 5

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 763552,4-HexanedioneHCID 189691746-amino-4-(3-bromophenyl)-1-ethyl-2(1H)-pyridone

生成物 1

HCID 99293314-(3-bromophenyl)-1,7-diethyl-5-methyl-1,8-naphthyridin-2(1H)-one収率 73%

反応条件

温度
140 °C

実験手順

A mixture of diphosphorus pentoxide (10.4 g) and phosphoric acid (5 ml) was stirred at 140° C. until it became transparent. Then, 6-amino-4-(3-bromophenyl)-1-ethyl-2(1H) -pyridone (2.5 g, 8.5 mmol) and 2,4-hexanedione (1.1 ml) were added to this solution, and the mixture was stirred at 140° C. for 3 hours. The reaction solution was poured into ice water, made alkaline by adding 1N sodium hydroxide aqueous solution and then extracted with ethyl acetate. After drying the organic layer with anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography (benzene-ethyl acetate) to give 4-(3-bromophenyl)-1,7-diethyl-5-methyl-1,8-naphthyridin-2(1H)-one (2.3 g, 73%).

後処理

  1. stirringthe mixture was stirred at 140° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialAfter drying the organic layer with anhydrous magnesium sulfate, magnesium sulfate
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was then purified by silica gel column chromatography (benzene-ethyl acetate)

出典と根拠

ORDレコード
ord-093ccdb530794f02ac1f966978b12bc8
出典データセット
uspto-grants-1998_10
特許番号
US05817670

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