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

HRID 1672217

反応式

HRID 1672217 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a663f48506b94ddf8c4235563cfe5c0c
出典データセット
uspto-grants-2011_08
特許番号
US07998952B2

関連ノート

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