Peracetic Acid → 2-(4-Ethoxycarbonylphenyl)pyridine N-oxide

HRID 280212노트

반응식

HRID 280212 반응식
C(OO)(=[O:3])C.[CH2:6]([O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:13][CH:12]=1)=[O:10])[CH3:7]>>[CH2:6]([O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N+:18]=2[O-:3])=[CH:13][CH:12]=1)=[O:10])[CH3:7]

참가 물질

3

반응물 2

HCID 6585Peracetic AcidHCID 14097203Ethyl 4-(pyridin-2-yl)benzoate

생성물 1

HCID 147974372-(4-Ethoxycarbonylphenyl)pyridine N-oxide

실험 절차

Peracetic acid (40%, 8.9 ml) is added dropwise to 2-(p-ethoxycarbonylphenyl)-pyridine (14.08 g) so as to maintain the reaction between 80° and 85°. After the addition is complete the reaction is heated at 90° for 3 hours, allowed to cool to room temperature and excess peracetic acid is destroyed with aqueous sodium sulfite. The solvent is evaporated and the residue taken up in methylene chloride and refiltered through celite. Evaporation yields 2-(p-ethoxycarbonylphenyl)pyridine-N-oxide which is treated with dimethyl sulfate (8.66 g) in 62 ml of toluene at 90° for 3 hours. The solvent is evaporated and the residue redissolved in an ice-cold mixture of 8 ml of water and 9.3 ml of 1N sodium hydroxide. A solution of potassium cyanide (13.64 g) in 10 ml of water is added slowly and the reaction mixture is maintained at 0° for 24 hours. Extraction with methylene chloride (2×30 ml), drying over sodium sulfate and evaporation of solvent yields 6-cyano-2-(p-ethoxycarbonylphenyl)pyridine; IR (CH2Cl2) 2200 cm-1.

후처리

  1. temperatureto maintain
  2. customthe reaction between 80° and 85°
  3. additionAfter the addition
  4. temperatureis heated at 90° for 3 hours
  5. customexcess peracetic acid is destroyed with aqueous sodium sulfite
  6. customThe solvent is evaporated
  7. customEvaporation

출처 및 근거

ORD 기록
ord-5843c6262ded4643b6139418813393a6
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588732

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