Pyridine → 7-Methyl-3-nitro-5,6,7,8-tetrahydroquinolin-5-one

HRID 346047노트

반응식

HRID 346047 반응식
[N+:1](C(C=O)C=O)([O-:3])=[O:2].[Na].[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S(Cl)(C1C=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=O)=O.CN(C)C=[O:30]>>[CH3:23][CH:22]1[CH2:24][C:15]2[N:10]=[CH:11][C:12]([N+:1]([O-:3])=[O:2])=[CH:13][C:14]=2[C:20](=[O:30])[CH2:21]1

참가 물질

5

반응물 4

HCID 1049PyridineHCID 6228Dimethylformamide2회HCID 73974-Toluenesulfonyl chlorideHCID 24193465CID 24193465

생성물 1

HCID 144227827-Methyl-3-nitro-5,6,7,8-tetrahydroquinolin-5-one

반응 조건

온도
-5 °C

실험 절차

Sodium nitromalonaldehyde (Org. Synth. Coll., vol. 4, p. 844; 42.4 g, 0.269 mol) was dissolved in 200 ml of dimethylformamide and the resulting solution dried over 4A-type molecular sieves, recovered by filtration with 100 ml of the same solvent for wash. To the combined filtrate and wash was added pyridine (91 ml, 89 g, 1.13 mol) and the mixture cooled to -5° C. Tosyl chloride (53 g, 0.277 mol) in 200 ml of dimethylformamide was added dropwise, maintaining a temperature of -5° to -8° C., and the reaction mixture allowed to warm to room temperature. The title product of the preceding Preparation (33.6 g, 0.270 mol), dissolved by warming in 200 ml of dimethylformamide and added in a steady stream to the reaction mixture, which was then stirred for 18 hours at room temperature, then poured into 2 liters of ice and water and extracted 2×1 liter of ethyl acetate. The organic layers wre combined, dried over MgSO and stripped to yield present title product, 33 g (61%), m.p. 64°-67° C.

후처리

  1. dry with materialthe resulting solution dried over 4A-type molecular sieves
  2. filtrationrecovered by filtration with 100 ml of the same solvent
  3. washfor wash
  4. washTo the combined filtrate and wash
  5. temperaturemaintaining a temperature of -5° to -8° C.
  6. temperatureto warm to room temperature

출처 및 근거

ORD 기록
ord-59338738c7924cbfa0ab248abda343cd
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05059609

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