Water → 2-(5-Amino-pyridin-2-yl)-malonic acid dibenzyl ester

HRID 858066노트

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HRID 858066 반응식
[CH2:1]([O:8][C:9](=[O:30])[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][N:22]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.O.[Cl-].[NH4+]>CO.[Zn]>[CH2:1]([O:8][C:9](=[O:30])[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][N:22]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 69115439Dibenzyl 5-nitro-2-pyridylmalonate

생성물 1

HCID 691148292-(5-Amino-pyridin-2-yl)-malonic acid dibenzyl ester수율 89%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

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온도
25 °C

실험 절차

A solution of 2-(5-nitro-pyridin-2-yl)-malonic acid dibenzyl ester in a mixture of methanol, tetrahydrofuran, and water was treated with ammonium chloride (25 eq.) and zinc dust (>10 micron,10 eq.). The mixture was stirred at 25° C. for 40 min. At this time, the reaction was filtered through celite. The filtrate was concentrated in vacuo. The aqueous residue was extracted with ethyl acetate. The organics were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2-(5-amino-pyridin-2-yl)-malonic acid dibenzyl ester as a yellow viscous oil (89%); LRMS for C22H20N2O4 (M+H)+ at m/z=377.

후처리

  1. filtrationAt this time, the reaction was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. extractionThe aqueous residue was extracted with ethyl acetate
  4. washThe organics were washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3a24a2b9009341c9976e16d3abb5ee36
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148229B2

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