Water → HCID 10797271, 화합물

HRID 2229305노트

반응식

HRID 2229305 반응식
Cl[Sn]Cl.O.[Cl:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][CH3:14])[C:9]([N+:15]([O-])=O)=[CH:8][CH:7]=1.O.[OH-].[Na+]>Cl.CC(O)=O>[NH2:15][C:9]1[C:10]([NH:12][CH2:13][CH3:14])=[N:11][C:6]([Cl:5])=[CH:7][CH:8]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 107267696-Chloro-N-ethyl-3-nitropyridin-2-amineHCID 43835034Tin dichloride dihydrate

생성물 1

HCID 10797271HCID 10797271, 화합물수율 62.4%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매

반응 조건

온도
0 °C

실험 절차

A solution of SnCl2.H2O (616.3 g, 2.73 mol) in aqueous 12 N HCl (500 mL) was rapidly added to a solution of 6-chloro-2-(ethylamino)-3-nitropyridine (169.5 g, 0.84 mol) in AcOH (1.7 L) at room temperature. After 20 min, the mixture was cooled to 0° C. and water (250 mL) was added. Solid NaOH (240 g) was then added in small portions. The resulting suspension was filtered to remove tin salts. The filtrate was diluted with water (3.5 L), the solution rendered basic by addition of aqueous 10 N NaOH and then extracted with EtOAc (3×1.7 L). The combined organic layers were washed with brine (1 L), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 3:2) to give the title compound (89.9 g, 62% yield) as a brown solid: MS (ESI) m/z 172/174 (MH)+.

후처리

  1. filtrationThe resulting suspension was filtered
  2. customto remove tin salts
  3. additionThe filtrate was diluted with water (3.5 L)
  4. additionthe solution rendered basic by addition of aqueous 10 N NaOH
  5. extractionextracted with EtOAc (3×1.7 L)
  6. washThe combined organic layers were washed with brine (1 L)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (hexane:EtOAc, 3:2)

출처 및 근거

ORD 기록
ord-46f38614edda4eb6be528a31ad0b3ddc
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06420359B1

반응 노트

불러오는 중…