Diethyl (formylamino)((2-nitrophenyl)methyl)propanedioate → Ethyl 3-(formylamino)-1,2,3,4-tetrahydro-2-oxo-3-quinolinecarboxylate

HRID 1648305

反応式

HRID 1648305 の反応式
[CH:1]([NH:3][C:4]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-])=O)([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5](OCC)=[O:6])=[O:2].[H][H]>[Pd].C(O)C>[CH:1]([NH:3][C:4]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:15][C:16]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:22][C:5]1=[O:6])=[O:2]

参加物

5

反応物 2

HCID 53819953Diethyl (formylamino)((2-nitrophenyl)methyl)propanedioateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 19919309Ethyl 3-(formylamino)-1,2,3,4-tetrahydro-2-oxo-3-quinolinecarboxylate収率 100.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of diethyl (formylamino)((2-nitrophenyl)methyl)propanedioate (8.54 g, 0.025 mol) and 10% palladium on carbon (2.0 g) in absolute ethanol (200 mL) was hydrogenated (50 lb initial H2 pressure) until hydrogen uptake ceased. The mixture was filtered through celite and refluxed for 2 hours to achieve cyclization. The solvent was removed under reduced pressure to give 6.6 g of product which was crystallized from methanol to give 5.0 g of white crystals, mp 187°-190° C. Anal. Calc'd for C13H14N2O4 : C, 59.53; H, 5.38; N, 10.68. Found: C, 59.77; H, 5.36; N, 10.75.

後処理

  1. filtrationThe mixture was filtered through celite
  2. temperaturerefluxed for 2 hours
  3. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-4145eba632d948abb33cafbaace9d028
出典データセット
uspto-grants-1995_07
特許番号
US05436240

関連ノート

読み込み中…