Water → HCID 11183484, 화합물

HRID 856631노트

반응식

HRID 856631 반응식
F[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)=[O:7])=[CH:4][CH:3]=1.[N-:17]=[N+]=[N-].[Na+].O>CS(C)=O>[NH2:17][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)[OH:7])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 113449352-(4-Fluorobenzoyl)-6-methylpyridine

생성물 1

HCID 11183484HCID 11183484, 화합물수율 72.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 2-(4-fluorobenzoyl)-6-methylpyridine (2.0 g) and sodium azide (3.36 g) in DMSO (40 ml) and the mixture was stirred for 24 hours at 90° C. To the reaction mixture was added water, and the mixture was extracted with diethylether. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and a solution of the residue (1.88 g) in THF (40 ml) was added dropwise to a suspension of aluminum lithium hydride (0.60 g) in. THF (20 ml) at 0° C. The mixture was stirred at room temperature for 30 minutes, and water (0.6 ml), 15% aqueous solution of sodium hydroxide (0.6 ml) and water (1.8 ml) were sequentially and slowly added dropwise to the solution at 0° C. The mixture was stirred at room temperature for 4 days, magnesium sulfate was added to the mixture, and the precipitates were removed by filtration (Celite). The reaction mixure was concentrated under reduced pressure, and the obtained residue was separated and purified by column chromatography (ethyl acetate), to give (4-aminophenyl)(6-methylpyridin-2-yl)methanol (1.44 g) as pale yellow crystals.

후처리

  1. extractionthe mixture was extracted with diethylether
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additiona solution of the residue (1.88 g) in THF (40 ml) was added dropwise to a suspension of aluminum lithium hydride (0.60 g) in
  6. customat 0° C
  7. additionslowly added dropwise to the solution at 0° C
  8. stirringThe mixture was stirred at room temperature for 4 days
  9. additionmagnesium sulfate was added to the mixture
  10. customthe precipitates were removed by filtration (Celite)
  11. concentrationThe reaction mixure was concentrated under reduced pressure
  12. customthe obtained residue was separated
  13. custompurified by column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-a8eae77bbe7440a7a27137c700b14c6e
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262185B2

반응 노트

불러오는 중…