Water → HCID 10797271、化合物

HRID 2229305ノート

反応式

HRID 2229305 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 10797271HCID 10797271、化合物収率 62.4%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-46f38614edda4eb6be528a31ad0b3ddc
出典データセット
uspto-grants-2002_07
特許番号
US06420359B1

反応ノート

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