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Dimethyl Sulfate → 6-Methyl-4-nitropyridine-2-carbonitrile

HRID 552481
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HRID 552481 반응식
COS(OC)(=O)=O.[CH3:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][N+:10]=1[O-].[C-:19]#[N:20].[K+]>O>[CH3:8][C:9]1[N:10]=[C:11]([C:19]#[N:20])[CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 9032Potassium CyanideHCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxide

생성물 1

HCID 113786726-Methyl-4-nitropyridine-2-carbonitrile수율 72.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

To 10.2 ml (13.5 g, 104 mmol, 1.1 equiv.) of dimethylsulfate were added 15.0 g (94.4 mmol) of 2-Methyl-4-nitropyridine-N-oxide at 60° C. The reaction mixture was then stirred for 90 min at 70° C., and allowed to cool to room temperature. The solidified residue was triturated with 30 ml of ether. The product was filtered, washed with 20 ml of ether, and dried. The product was then dissolved in 100 ml of water and added dropwise over a period of 30 min. to a at −8° C. cooled solution of 24.6 g (377 mmol, 4.0 equiv.) of potassium cyanide in 100 ml of water. The reaction mixture was stirred for a further 15 min. at −8° C. The product was filtered off, washed twice with 15 ml of water and dried in vaccuo to yield the title compound (11.1 g, 72%) as a light brown solid.

후처리

  1. temperatureto cool to room temperature
  2. customThe solidified residue was triturated with 30 ml of ether
  3. filtrationThe product was filtered
  4. washwashed with 20 ml of ether
  5. customdried
  6. dissolutionThe product was then dissolved in 100 ml of water
  7. additionadded dropwise over a period of 30 min. to a at −8° C.
  8. stirringThe reaction mixture was stirred for a further 15 min. at −8° C
  9. filtrationThe product was filtered off
  10. washwashed twice with 15 ml of water
  11. customdried in vaccuo

출처 및 근거

ORD 기록
ord-aec1ee2be0a8485ba15c4cd514d0d343
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951824B2

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