Dimethylformamide → 6-(Cyclopentyloxy)pyridin-3-amine

HRID 1294829노트

반응식

HRID 1294829 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[N:8][CH:9]=1)([O-])=O.Br[CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH:12]1([O:10][C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 178526703HCID 178526703, 화합물

생성물 1

HCID 167909726-(Cyclopentyloxy)pyridin-3-amine

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of 5-nitropyridin-2-ol (14.0 g), bromocyclopentane (8.0 g), potassium carbonate (14 g) and DMF (200 mL) was heated at 80° C. for 6 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel. The resulting product (2-cyclopentyloxy-5-nitropyridine) was hydrogenated in ethanol using palladium(II) hydroxide as catalyst. The product with the molecular weight of 178.24 (C10H14N20) was obtained in this way; MS (ESI): 179 (M+H+).

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. customThe product with the molecular weight of 178.24 (C10H14N20) was obtained in this way

출처 및 근거

ORD 기록
ord-dd01796d942645b594afdabc12631e92
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241787B2

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