Reaction equation
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]=1Participants
Conditions
- Temperature
- 140 °C
Procedure
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%).
Workup
- stirringthe mixture was stirred at 140° C. for 3 hours
- extractionextracted with ethyl acetate
- dry with materialAfter drying the organic layer with anhydrous magnesium sulfate, magnesium sulfate
- customwas removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe resulting residue was then purified by silica gel column chromatography (benzene-ethyl acetate)
Sources & evidence
- ORD record
- ord-093ccdb530794f02ac1f966978b12bc8
- Source dataset
- uspto-grants-1998_10
- Patent number
- US05817670
Linked notes
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