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

HRID 1871669ノート

反応式

HRID 1871669 の反応式
[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]

参加物

5

反応物 2

HCID 7242O-ToluidineHCID 707902,6-Diacetylpyridine

生成物 1

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

試薬・触媒・溶媒 2

HCID 284Formic Acid触媒HCID 6344Dichloromethane溶媒

実験手順

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): δ 8.38(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).

後処理

  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

出典と根拠

ORDレコード
ord-c556502c9b2743b691550ce78ab09eb1
出典データセット
uspto-grants-2000_08
特許番号
US06103946

反応ノート

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