Acetyl chloride → 2-Acetamido-6-aminopyridine

HRID 1716904

반응식

HRID 1716904 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[C:9](Cl)(=[O:11])[CH3:10]>O1CCOCC1>[NH2:8][C:4]1[N:3]=[C:2]([NH:1][C:9](=[O:11])[CH3:10])[CH:7]=[CH:6][CH:5]=1

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 88612,6-Diaminopyridine

생성물 1

HCID 37673452-Acetamido-6-aminopyridine수율 76.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
0 °C

실험 절차

Dissolve 2,6-diaminopyridine (9.822 g, 90 mmol) in dioxane (100 mL) and cool to 0° C. Add acetyl chloride (2.355 g, 2.1 mL, 30 mmol) slowly and stir for 1 hr. at 0° C. Remove the ice bath and stir at room temperature overnight. Quench the reaction mixture with saturated NaHCO3 solution, extract with ethyl acetate three times. Combine the organic layers, dry over Na2SO4, filter, and concentrate to give a solid. Chromatography on silica gel, eluting with a gradient of 60-70% ethylacetate in hexanes affords the title intermediate (3.45 g, 76%): mass spectrum (ion spray): m/z=152.1 (M+1); 1H NMR (CDCl3, ppm): 7.49 (m, 3H), 6.28 (d, 1H), 4.31 (s, br, 2H), 2.19 (s, 3H).

후처리

  1. customat 0° C
  2. customRemove the ice bath
  3. customQuench the reaction mixture with saturated NaHCO3 solution
  4. extractionextract with ethyl acetate three times
  5. dry with materialCombine the organic layers, dry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give a solid
  9. washChromatography on silica gel, eluting with a gradient of 60-70% ethylacetate in hexanes

출처 및 근거

ORD 기록
ord-cbc107f8ed8c4b09a436742786952ccd
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803813B2

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