Ethanol → Methyl 3-amino-5-[(dipropylamino)carbonyl]Benzoate

HRID 852563

反応式

HRID 852563 の反応式
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[C:6]([C:7]([N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.CCO>[Pd].O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:18]=[C:17]([NH2:19])[CH:16]=[C:6]([C:7]([N:9]([CH2:10][CH2:11][CH3:12])[CH2:13][CH2:14][CH3:15])=[O:8])[CH:5]=1

参加物

5

反応物 2

HCID 702EthanolHCID 690570Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate

生成物 1

HCID 22593627Methyl 3-amino-5-[(dipropylamino)carbonyl]Benzoate収率 88%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A mixture of 5-nitro-N,N-dipropyl-isophthalamic acid methyl ester (D87) (1.5 g, 4.9 mmol, 1 equiv), NH4COOH (3.0 g, 49 mmol, 10 equiv), 10% Pd on charcoal (50% wet, 250 mg, 0.082 equiv w/w), EtOH (20 ml) and H2O (10 ml) was heated at 50° C. for 90 min. The mixture was cooled to room temperature, filtered through a pad of celite and concentrated in vacuo. The residue was dissolved in AcOEt (200 ml) and the resulting solution was washed with saturated NaHCO3 solution (100 ml), dried over MgSO4 and concentrated in vacuo to give 5-amino-N,N-dipropyl-isophthalamic acid methyl ester (D88) (1.2 g, 88%) as a white waxy solid.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in AcOEt (200 ml)
  5. washthe resulting solution was washed with saturated NaHCO3 solution (100 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-82322feba5904310bcdc5ebb0194cf1a
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

関連ノート

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