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

HRID 398835

반응식

HRID 398835 반응식
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

참가 물질

6

반응물 5

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

생성물 1

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

반응 조건

온도
140 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-093ccdb530794f02ac1f966978b12bc8
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817670

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