Triethylamine → 2-[3-[3-[(E)-3-(2-pyridyl)acryloylamino]phenyl]phenylamino]-3-nitropyridine

HRID 1953411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953411
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]([OH:11])=O.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[NH2:26][C:27]1[CH:28]=[C:29]([C:33]2[CH:34]=[C:35]([NH:39][C:40]3[C:45]([N+:46]([O-:48])=[O:47])=[CH:44][CH:43]=[CH:42][N:41]=3)[CH:36]=[CH:37][CH:38]=2)[CH:30]=[CH:31][CH:32]=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]([NH:26][C:27]1[CH:28]=[C:29]([C:33]2[CH:34]=[C:35]([NH:39][C:40]3[C:45]([N+:46]([O-:48])=[O:47])=[CH:44][CH:43]=[CH:42][N:41]=3)[CH:36]=[CH:37][CH:38]=2)[CH:30]=[CH:31][CH:32]=1)=[O:11]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 2478243-(2-Pyridyl)acrylic acidHCID 232981392-[3-(3-Aminophenyl)phenylamino]-3-nitropyridine

Produkt 1

HCID 232981322-[3-[3-[(E)-3-(2-pyridyl)acryloylamino]phenyl]phenylamino]-3-nitropyridineAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice cooled suspension of 3-(2-pyridyl)acrylic acid (1.07 g) in dry methylene chloride (80 ml) was added triethylamine (1.46 g) and pivaloyl chloride (0.87 g) and the mixture was stirred for 2 hours. After the clear reaction mixture was obtained, 2-[3-(3-aminophenyl)phenylamino]-3-nitropyridine (2.0 g) was added thereto and stirred under reflux overnight. The reaction was chromatographed on silica gel (chloroform-methanol 50:1 as an eluent) to give 2-[3-[3-[(E)-3-(2-pyridyl)acryloylamino]phenyl]phenylamino]-3-nitropyridine as an orange crystal (2.85 g).

Aufarbeitung

  1. customAfter the clear reaction mixture was obtained
  2. stirringstirred
  3. temperatureunder reflux overnight
  4. customThe reaction was chromatographed on silica gel (chloroform-methanol 50:1 as an eluent)

Quellen und Nachweise

ORD-Eintrag
ord-87af4c75deaf41fcb24a63da7689739f
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06117875

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