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

HRID 1953411Notes

Reaction equation

HRID 1953411 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 232981322-[3-[3-[(E)-3-(2-pyridyl)acryloylamino]phenyl]phenylamino]-3-nitropyridineYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-87af4c75deaf41fcb24a63da7689739f
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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