Dimethylformamide → 4-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile

HRID 1935030ノート

反応式

HRID 1935030 の反応式
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=O)[C:9]([C:14]#[N:15])=[CH:10][NH:11]2)=[CH:6][C:5]=1[O:17][CH3:18])[CH3:2].C(Cl)(=O)C([Cl:22])=O.CN(C=O)C.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+].C(Cl)Cl>[Cl:22][C:8]1[C:7]2[C:12](=[CH:13][C:4]([O:3][CH2:1][CH3:2])=[C:5]([O:17][CH3:18])[CH:6]=2)[N:11]=[CH:10][C:9]=1[C:14]#[N:15]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 65578Oxalyl chlorideHCID 104904723-Quinolinecarbonitrile, 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-

生成物 1

HCID 105634734-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile収率 89.1%

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Mixed 122 mg (0.50 mmol) 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-3-quinolinecarbonitrile and 2.0 ml methylene chloride under N2 and kept temperature near 25° C. Added 218 μl (2.5 mmol) oxalyl chloride and 10 μl (0.125 mmol) DMF. Stirred overnight, diluted with chloroform and stirred in saturated sodium bicarbonate until basic. Separated layers and dried organics with magnesium sulfate, stripped solvent and dried in vacuo, giving 117 mg of tan solid: mass spectrum (electrospray m/e): M+H=262.8, 264.8.

後処理

  1. customnear 25° C
  2. customdried in vacuo

出典と根拠

ORDレコード
ord-d1c9290b9ee34a7bb5392bdb1686107f
出典データセット
uspto-grants-2002_05
特許番号
US06384051B1

反応ノート

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