Ammonium Chloride → 2-methyl-3,4,5,6-tetrafluoropyridine N-oxide

HRID 1869

반응식

HRID 1869 반응식
F[C:2]1C(F)=C(F)C(F)=C(F)N=1.F[C:13]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[N+:14]=1[O-:23].C[Mg]I.[Cl-].[NH4+]>C(OCC)C>[CH3:2][C:13]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[N+:14]=1[O-:23]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 69690PentafluoropyridineHCID 536887372,3,4,5,6-pentafluoropyridine N-oxideHCID 178418373HCID 178418373, 화합물

생성물 1

HCID 702851192-methyl-3,4,5,6-tetrafluoropyridine N-oxide

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

2,3,4,5,6-Pentafluoropyridine (commercially available from Aldich Chemical Co.) is oxidized to the corresponding N-oxide following the procedures described in Step 6 of Example 66. The 2,3,4,5,6-pentafluoropyridine N-oxide is treated at ambient temperature with one equivalent of methylmagnesium iodide in diethyl ether as described by F. Binns and H. Suschitsky in Chemical Communications, 750-751 (1970) and J Chem Soc (C), 1223-1231 (1771). The reaction mixture is treated with aqueous ammonium chloride and extracted with diethyl ether. The ether solution is dried over anhydrous magnesium sulfate, filtered and concentated under reduced pressure and the crude product is chromatographed on silica gel to afford 2-methyl-3,4,5,6-tetrafluoropyridine N-oxide (3,4,5,6-tetrafluoro-2-picoline). The N-oxide is then reduced to afford the title compound by the procedures described in Step 8 of Example 66.

후처리

  1. extractionextracted with diethyl ether
  2. dry with materialThe ether solution is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe crude product is chromatographed on silica gel

출처 및 근거

ORD 기록
ord-d1624c7c809f4abaa8b97cad497ea554
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726182

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