Morpholine → 4-(6-Methyl-5-nitro-2-pyridinyl)morpholine

HRID 2388008

반응식

HRID 2388008 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:11][C:4]1[N:3]=[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 124081856-Fluoro-2-methyl-3-nitropyridine

생성물 1

HCID 82089554-(6-Methyl-5-nitro-2-pyridinyl)morpholine수율 99%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
70 °C

실험 절차

To a solution of 2-fluoro-5-nitro-6-picoline (3.0 g, 19.2 mmol) in DMSO (26 mL) were added morpholine (3.35 mL, 38.4 mmol) and potassium carbonate (6.64 g, 48.0 mmol). The reaction mixture was allowed to stir overnight, at 70° C. The reaction mixture was then partitioned between EtOAc (40 mL) and water (40 mL). The organic solution was separated and the aqueous solution was extracted with EtOAc (2×40 mL). The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated to give 4-(6-methyl-5-nitropyridin-2-yl)morpholine (4.0 g, 99%), as a muddy green solid. LCMS (FA): Rt=1.59 min, m/z=224.0 (M+H).

후처리

  1. customThe reaction mixture was then partitioned between EtOAc (40 mL) and water (40 mL)
  2. customThe organic solution was separated
  3. extractionthe aqueous solution was extracted with EtOAc (2×40 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-06856b0ed9c843d68bf56fab76e05399
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268992B2

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