2-Chloro-3-methyl-5-nitropyridine → 6-Chloro-5-methylpyridin-3-amine

HRID 367065

반응식

HRID 367065 반응식
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>O.CC(O)=O.[Fe]>[NH2:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Cl:1])=[N:3][CH:4]=1

참가 물질

4

반응물 1

HCID 896482-Chloro-3-methyl-5-nitropyridine

생성물 1

HCID 122956076-Chloro-5-methylpyridin-3-amine수율 89%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 21899381Acetic acid--water (1/1)용매

실험 절차

2-Chloro-3-methyl-5-nitropyridine (3.2 g, 18.5 mmol; Maybridge Chemical Co.) was dissolved in a mechanically stirred solution of H2O/HOAc (60 mL, 5:1). Iron powder was added over a 5 h period, maintaining the temperature below 40° C., and stirring was continued until starting material had be consumed. The reaction mixture was filtered, and the filter cake was washed with EtOAc. The aqueous filtrate was extracted with EtOAc, and the combined organic fractions were washed with saturated NaHCO3 solution, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; CHCl3 /MeOH, 98:2) to afford 5-amino-2-chloro-3-methylpyridine as an orange solid (2.34 g, 89%): MS (CI/NH3) m/z: 143 (M+H)+ ; NMR (DMSO-d6, 300 MHz) δ 2.17 (s, 3H), 5.40 (br s, 2H), 6.90 (d, J=2.2 Hz, 1H), 7.54 (d, J=2.2 Hz, 1H).

후처리

  1. temperaturemaintaining the temperature below 40° C.
  2. customhad be consumed
  3. filtrationThe reaction mixture was filtered
  4. washthe filter cake was washed with EtOAc
  5. extractionThe aqueous filtrate was extracted with EtOAc
  6. washthe combined organic fractions were washed with saturated NaHCO3 solution
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was chromatographed (silica gel; CHCl3 /MeOH, 98:2)

출처 및 근거

ORD 기록
ord-08df4e70870c43d5bdb28521a8e5eee0
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133253

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