Pyridine → HCID 10829037, compound

HRID 234280Notes

Reaction equation

HRID 234280 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[C:13](=O)[C:12]([CH3:15])=[C:11]([CH3:16])[C:10](=[O:17])[C:9]=1[CH2:18][C:19]([CH3:21])=[CH2:20].[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>ClCCCl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([N:27]=[C:13]2[C:12]([CH3:15])=[C:11]([CH3:16])[C:10](=[O:17])[C:9]([CH2:18][C:19]([CH3:21])=[CH2:20])=[C:8]2[CH3:7])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 78124-ChloroanilineHCID 3188402,3,5-Trimethyl-6-(2-methylprop-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione

Product 1

HCID 10829037HCID 10829037, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

Titanium tetrachloride (2.42 ml, 22.1 mmol) was added dropwise to a solution of pyridine (7.13 ml, 88.2 mmol) in 1,2-dichloroethane (40 ml) and, after completion of addition, the reaction mixture was heated under reflux minutes in an argon atmosphere. After cooling of the reaction mixture, to the mixture was added a solution of 3,5,6-trimethyl-2-(2-methyl-2-propenyl)-1,4-benzoquinone (3.00 g, 14.7 mmol) and p-chloroaniline (5.62 g, 44.1 mmol) in 1,2-dichloroenhane (20 ml) and the mixture was stirred 90° C. for 45 minutes in an argon atmosphere. The reaction mixture was cooled and filtered through Cerite and the filtrate was washed with a saturated saline solution, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate, 93:7) to obtain the desired compound as oil (4.43 g, yield: 96.0%).

Workup

  1. additionafter completion of addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux minutes in an argon atmosphere
  4. temperatureAfter cooling of the reaction mixture, to the mixture
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered through Cerite
  7. washthe filtrate was washed with a saturated saline solution
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate, 93:7)

Sources & evidence

ORD record
ord-a08b7c6307b54c0da120ce99876fcd06
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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