Methanol → 4-(2,3-Dichloro-6-fluorophenyl)-1,4,5,6,7,8-hexahydro-2-methyl-7-phenyl-methyl-5-oxo-1,7-naphthyridine-3-carboxylic acid 2-(2,3-dichlorophenoxy)ethyl ester

HRID 2290838

反応式

HRID 2290838 の反応式
O.[CH2:2]([N:9]1[CH2:14][C:13](=O)[CH2:12][CH:11]([OH:16])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5]C=1.[Cl:17][C:18]1[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([F:27])[C:19]=1[CH:20]=O.[C:28]([O:34][CH2:35][CH2:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[C:39]=1[Cl:45])(=[O:33])[CH2:29][C:30]([CH3:32])=O.C([O-])(=O)C.[NH4+:50].[CH3:51]O>>[Cl:45][C:39]1[C:40]([Cl:44])=[CH:41][CH:42]=[CH:43][C:38]=1[O:37][CH2:36][CH2:35][O:34][C:28]([C:29]1[CH:20]([C:19]2[C:22]([F:27])=[CH:23][CH:24]=[C:25]([Cl:26])[C:18]=2[Cl:17])[C:12]2[C:11](=[O:16])[CH2:10][N:9]([C:2]3[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:14][C:13]=2[N:50]([CH3:51])[C:30]=1[CH3:32])=[O:33]

参加物

6

反応物 5

HCID 887MethanolHCID 517165Ammonium AcetateHCID 32600622,3-Dichloro-6-fluorobenzaldehydeHCID 136697262-(2,3-Dichlorophenoxy)ethyl acetoacetateHCID 202306231-Benzyl-3-hydroxy-5-oxo-1,2,3,6-tetrahydropyridine hydrate

生成物 1

HCID 704556114-(2,3-Dichloro-6-fluorophenyl)-1,4,5,6,7,8-hexahydro-2-methyl-7-phenyl-methyl-5-oxo-1,7-naphthyridine-3-carboxylic acid 2-(2,3-dichlorophenoxy)ethyl ester収率 52.3%

実験手順

Methanol (400 ml), 22.1 g (0.1 mole) of 1-benzyl-3-hydroxy-5-oxo-1,2,3,6-tetrahydropyridine hydrate, 19.3 g (0.1 mole) of 2,3-dichloro-6-fluorobenzaldehyde, 29.1 g (0.1 mole) of 2-(2,3-dichlorophenoxy)ethyl acetoacetate and 16 g (0.21 mole) of ammonium acetate were combined and heated to reflux. Solid began to precipitate after one-half hour, but refluxing was continued for 4 hours. The mixture was cooled to room temperature and filtered. The solid was washed with methanol, then dried in vacuo to obtain 34 grams (52.3%) of 4-(2,3-Dichloro-6-fluorophenyl)-1,4,5,6,7,8-hexahydro-2-methyl-7-phenyl-methyl-5-oxo-1,7-naphthyridine-3-carboxylic acid 2-(2,3-dichlorophenoxy)ethyl ester, m.p. 204°-6° C.

後処理

  1. temperatureheated to reflux
  2. customto precipitate after one-half hour
  3. temperaturerefluxing
  4. filtrationfiltered
  5. washThe solid was washed with methanol
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-785b0c75440449d08ce5cc7fd6aa5227
出典データセット
uspto-grants-1986_10
特許番号
US04618678

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