醋酸 → 4-甲基-3-氨基-2-氟吡啶

HRID 2396689

反应方程式

HRID 2396689 反应方程式
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.C(O)(=O)C.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:8][C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][C:6]=1[CH3:11]

参与物

6

反应物 3

HCID 176醋酸HCID 124081822-氟-3-硝基-4-甲基吡啶HCID 178418361HCID 178418361，化合物

产物 1

HCID 27631614-甲基-3-氨基-2-氟吡啶

试剂、催化剂与溶剂 2

HCID 23938钯催化剂HCID 8857乙酸乙酯溶剂

实验过程

To a solution of 10.1 g (65 mmol) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge) (2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was recovered, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid melting at 63°-64° C. Nuclear Magnetic Resonance Spectrum (200 MHz (megaHertz), CDCl3): 1H: 7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13C: 152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5); 128.1 (d, J=27.1); 123.3, 16.4 (d, J=4.1).

后处理

  1. filtrationwas filtered
  2. concentrationwas concentrated by evaporation under reduced pressure
  3. customto obtain an oil
  4. customThis oil was partitioned between dilute aqueous sodium bicarbonate and ether
  5. customThe organic phase was recovered
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  9. customthe residue was purified by column chromatography

来源与证据

ORD记录
ord-1ed7934d9cfd48d4b2386596551a3285
来源数据集
uspto-grants-1996_02
专利号
US05494887

关联笔记

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