Acetic Acid → 2-Fluoro-4-methylpyridin-3-amine

HRID 2396689

반응식

HRID 2396689 반응식
[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]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 124081822-Fluoro-4-methyl-3-nitropyridineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 27631612-Fluoro-4-methylpyridin-3-amine

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1ed7934d9cfd48d4b2386596551a3285
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05494887

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