Tetrahydrofuran → 4-Chloro-N-methyl-3-nitropyridin-2-amine

HRID 1864670ノート

反応式

HRID 1864670 の反応式
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH2:14]1COCC1>>[Cl:11][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][CH3:14])[C:7]=1[N+:8]([O-:10])=[O:9]

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 40716944-Chloro-3-nitropyridin-2-amine

生成物 1

HCID 249031234-Chloro-N-methyl-3-nitropyridin-2-amine収率 25%

反応条件

温度
0 °C

実験手順

2-Amino-4-chloro-3-nitropyridine (590 mg, 4 mmol) was dissolved in dry THF (15 mL), the solution was cooled to 0° C. and NaH (240 mg, 6 mmol) was added. The reaction mixture was stirred for 2 hours, and allowed to warm at room temperature. The solvent was evaporated and the residue extracted between AcOEt and water. The organic layer was dried (MgSO4) and evaporated. The crude mixture was purified by column chromatography (eluent DCM) to afford the title compound (190 mg, 25%). 1H-NMR (6, ppm, DMSO-d6): 2.88 (d, 3H, Me, J=4.55 Hz), 6.86 (d, 1H, HPy,5, J=5.31 Hz), 7.44 (broad s, 1H, NH), 8.21 (d, 1H, HPy,5, J=5.30 Hz).

後処理

  1. temperatureto warm at room temperature
  2. customThe solvent was evaporated
  3. extractionthe residue extracted between AcOEt and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customThe crude mixture was purified by column chromatography (eluent DCM)

出典と根拠

ORDレコード
ord-c2c06492e30a4a2eb9ed491907206444
出典データセット
uspto-grants-2009_12
特許番号
US07625922B2

反応ノート

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