Ammonia → 6-Chloro-3-nitropyridin-2-ylamine

HRID 25863

反応式

HRID 25863 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.CCO.O.[NH3:16]>>[Cl:11][C:4]1[N:3]=[C:2]([NH2:16])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

参加物

5

反応物 4

HCID 222AmmoniaHCID 702EthanolHCID 962WaterHCID 852392,6-Dichloro-3-nitropyridine

生成物 1

HCID 27240356-Chloro-3-nitropyridin-2-ylamine収率 89%

実験手順

2,6-Dichloro-3-nitropyridine 90 (10.0 g, 51.8 mmol) was dissolved in 37 ml of a 7N solution of NH3 in EtOH (0.26 mol, 5.0 eqv) and the solution was stirred at rt for 24 h. H2O (40 ml) was added and the resulting mixture was filtered to collect the crude yellow product. The solid material was dissolved in CH2Cl2 and then extracted with a 1N HCl solution. The aqueous extracts were combined and then neutralized with NaHCO3 before being re-extracted with CH2Cl2. The organic fractions were combined, dried (MgSO4), filtered, and concentrated in vacuo to yield 8.0 g of a yellow solid (89%): 1H NMR (400 MHz, d6-DMSO) d 6.77 (d, J=8.8 Hz, 1H), 8.27 (s, 2H), 8.39 (d, J=8.4 Hz, 1H); 13C NMR (125 MHz, d6-DMSO) d 111.89, 126.02, 138.28, 153.36, 154.88; HRMS (EI) Calcd for C5H4ClN3O2: 172.9997. Found 172.9996.

後処理

  1. filtrationthe resulting mixture was filtered
  2. customto collect the crude yellow product
  3. dissolutionThe solid material was dissolved in CH2Cl2
  4. extractionextracted with a 1N HCl solution
  5. extractionbefore being re-extracted with CH2Cl2
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c508e66893ef4c08bd21193572dff79f
出典データセット
uspto-grants-2005_02
特許番号
US06858600B2

関連ノート

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