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Triethylamine → 1-Nicotinoyl-3-phenyl-1,4,5,6-tetrahydropyridazine

HRID 2307259
Notes
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Reaction equation

HRID 2307259 reaction equation
[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:14]([N:9]1[CH2:10][CH2:11][CH2:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 106785433-phenyl-1,4,5,6-tetrahydropyridazine

Product 1

HCID 98565971-Nicotinoyl-3-phenyl-1,4,5,6-tetrahydropyridazineYield 46.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Phenyl-1,4,5,6-tetrahydropyridazine (2.4 g) synthesized in Reference Example 1 was dissolved in chloroform (50 ml). Thereto were added nicotinic acid chloride hydrochloride (2.6 g) and triethylamine (3.2 g) with ice-cooling. Stirring was conducted for 30 minutes. The reaction mixture was washed with water, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography to obtain 1.8 g of a title compound.

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-256cf26e12014ca682e793502cf1d3df
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06831083B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes