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

HRID 398840

反応式

HRID 398840 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]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:22]=1.[CH3:36][C:37](=O)[CH2:38][C:39](=O)[CH2:40][CH3:41].[OH-].[Na+]>>[CH:30]1([C:23]2[C:22]3[C:21](=[N:20][C:39]([CH2:40][CH3:41])=[CH:38][C:37]=3[CH3:36])[N:26]([CH2:27][CH3:28])[C:25](=[O:29])[CH:24]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

参加物

6

反応物 5

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 763552,4-HexanedioneHCID 189692166-amino-4-cyclohexyl-1-ethyl-2(1H)-pyridone

生成物 1

HCID 189691894-cyclohexyl-1,7-diethyl-5-methyl-1,8-naphthyridin-2(1H)-one

反応条件

温度
140 °C

実験手順

A mixture of 5.0 g of diphosphorus pentoxide and 2.5 ml of phosphoric acid was stirred at 140° C. until it became transparent. Then, 1.1 g of 6-amino-4-cyclohexyl-1-ethyl-2(1H)-pyridone and 0.6 ml of 2,4-hexanedione 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 1 N sodium hydroxide aqueous solution and then extracted with ethyl acetate. After drying the ethyl acetate layer over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (toluene-ethyl acetate) to give 1.2 g of 4-cyclohexyl-1,7-diethyl-5-methyl-1,8-naphthyridin-2(1H)-one.

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 ethyl acetate layer over anhydrous magnesium sulfate, magnesium sulfate
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was then purified by silica gel column chromatography (toluene-ethyl acetate)

出典と根拠

ORDレコード
ord-416e61b81e344a528749ac9bcb03a80d
出典データセット
uspto-grants-1998_10
特許番号
US05817670

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