Dimethylformamide → HCID 87235355、化合物

HRID 2194495ノート

反応式

HRID 2194495 の反応式
[O:1]=[C:2]1[C:11]([C:12](O)=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)(=O)C([Cl:24])=O.CN(C)C=O>ClCCl>[O:1]=[C:2]1[C:11]([C:12]([Cl:24])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 534020662-Oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

生成物 1

HCID 87235355HCID 87235355、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

1.62 g (6.1 mmol) of 2-oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid was dissolved in dichloromethane (60 mL), and 3.7 mL (44 mmol) of oxalyl chloride was added thereto. One droplet of N,N-dimethylformamide was added to the above mixture, and the resulting mixture was stirred for one hour at 40° C. The reaction mixture was concentrated under reduced pressure, and thus 2-oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid chloride was obtained. The acid chloride thus obtained was dissolved in dichloromethane (60 mL), and 0.75 g (6.7 mmol) of 1,3-cyclohexanedione and 1.03 mL (7.3 mmol) of triethylamine were added to the above solution. The resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into an aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with dichloromethane. The organic phase was dried and concentrated. The residue was washed with diisopropyl ether, and thus 2.16 g (yield: 99%) of the title compound was obtained as a light yellow solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-073521c806cd49998d2b3df577726de9
出典データセット
uspto-grants-2012_12
特許番号
US08334236B2

反応ノート

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