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

HRID 852563

반응식

HRID 852563 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-82322feba5904310bcdc5ebb0194cf1a
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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