Diethyl (formylamino)(8-quinolinylmethyl)malonate → ethyl 2,3,6,7-tetrahydro-3-oxo-2-(formylamino)-1H,5H-benzo(ij)quinolizine-2-carboxylate

HRID 327437ノート

反応式

HRID 327437 の反応式
[CH:1]([NH:3][C:4]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)([C:10](OCC)=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:2].[H][H]>C(O)(=O)C.[Pt]=O>[O:11]=[C:10]1[C:4]([NH:3][CH:1]=[O:2])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:15][C:16]2=[CH:17][CH:18]=[CH:19][C:20]3=[C:25]2[N:24]1[CH2:23][CH2:22][CH2:21]3

参加物

5

反応物 2

HCID 54322974Diethyl (formylamino)(8-quinolinylmethyl)malonateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86747427ethyl 2,3,6,7-tetrahydro-3-oxo-2-(formylamino)-1H,5H-benzo(ij)quinolizine-2-carboxylate収率 97%

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 176Acetic Acid溶媒

実験手順

A mixture of diethyl (formylamino)(8-quinolinylmethyl)malonate (9.2 g, 26.7 mmol) and platinum oxide (0.7 g) in glacial acetic acid (150 mL) was hydrogenated (50 lb initial pressure) for 15 minutes (hydrogen uptake ca. 2 equiv). The mixture was filtered through celite and the solvent removed under reduced pressure. The product was partitioned between ethyl acetate and sodium hydroxide solution. The ethyl acetate phase was washed with water, the ethyl acetate was evaporated, and the product was crystallized from ether to give 7.8 g (97%) of ethyl 2,3,6,7-tetrahydro-3-oxo-2-(formylamino)-1H,5H-benzo(ij)quinolizine-2-carboxylate, mp 103°-106° C. Anal. Calcd. for C16H18N2O4 : C, 63.56; H, 6.00; N, 9.27. Found: C, 63.51; H, 6.09; N, 9.18.

後処理

  1. customfor 15 minutes
  2. filtrationThe mixture was filtered through celite
  3. customthe solvent removed under reduced pressure
  4. customThe product was partitioned between ethyl acetate and sodium hydroxide solution
  5. washThe ethyl acetate phase was washed with water
  6. customthe ethyl acetate was evaporated
  7. customthe product was crystallized from ether

出典と根拠

ORDレコード
ord-304c9e242c2a4b39a9fc76d7aa0fcdf5
出典データセット
uspto-grants-1993_12
特許番号
US05273975

反応ノート

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