O-Toluidine → 2,6-Bis[1-(2-methylphenylimino)ethyl]pyridine

HRID 1583050노트

반응식

HRID 1583050 반응식
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=O)[CH3:2].[NH2:13][C:14]1[C:15]([CH3:20])=[CH:16][CH:17]=[CH:18][CH:19]=1>C(O)=O.C(Cl)Cl>[CH3:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:13]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[N:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH3:11])[N:5]=1)[CH3:2]

참가 물질

5

반응물 2

HCID 7242O-ToluidineHCID 707902,6-Diacetylpyridine

생성물 1

HCID 112719622,6-Bis[1-(2-methylphenylimino)ethyl]pyridine수율 45.9%

시약·촉매·용매 2

HCID 284Formic Acid촉매HCID 6344Dichloromethane용매

실험 절차

One g of 2,6-diacetylpyridine and 3.0 ml of o-toluidine were added to an Erlenmeyer flask with 20 ml of methylene chloride. A stirbar and 5 drops of 97% formic acid were added, and the flask was sealed and the solution was stirred for 40 hours. The solvent was then removed in vacuo, and the flask was placed in the freezer at −30° C. The resulting viscous oil was washed with cold methanol, and a yellow solid formed and was isolated by filtration and identified by 1H NMR as the desired product (959 mg, 45.9%). 1H NMR (CDCl3): δ8.38(d, 2, Hpyr) 7.86(t, 1, Hpyr), 7.20(m, 4, Haryl) 7.00(t, 2, Haryl), 6.67(d, 2, Haryl) 2.32 (s, 6, N═C—CH3) 2.10(s, 6, CH3 aryl).

후처리

  1. customthe flask was sealed
  2. customThe solvent was then removed in vacuo
  3. customwas placed in the freezer at −30° C
  4. washThe resulting viscous oil was washed with cold methanol
  5. customa yellow solid formed
  6. customwas isolated by filtration

출처 및 근거

ORD 기록
ord-0dae5810af784418bfc161e22e9e7abf
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06740715B2

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