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

HRID 1648305

반응식

HRID 1648305 반응식
[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]

참가 물질

5

반응물 2

HCID 53819953Diethyl (formylamino)((2-nitrophenyl)methyl)propanedioateHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4145eba632d948abb33cafbaace9d028
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05436240

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