m,alpha-Dichlorotoluene → 3-(2-(3-Chlorophenyl)ethyl)-N-(1,1-dimethylethyl)-2-pyridinecarboxamide

HRID 542759

Reaction equation

[CH3:1][C:2]([NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[Br-].[Na+].[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Cl>O1CCCC1.CCCCCC.O>[Cl:22][C:23]1[CH:24]=[C:25]([CH2:26][CH2:14][C:13]2[C:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: -40 °C

Procedure

31.5 g of N-(1,1-dimethylethyl)-3-methyl-2-pyridine carboxamide (e.g., as prepared in step A of Example I above) is dissolved in 600 mL of dry tetrahydrofuran and the resulting solution is cooled to -40° C. Two equivalents of n-butyllithium in hexane are added while the temperature is maintained at -40° C. The solution turned deep purple-red. 1.6 g of sodium bromide is added and the mixture is stirred. A solution of 26.5 g (0.174 mole) m-chlorobenzylchloride in 125 mL of tetrahydrofuran is added while the temperature is maintained at -40° C. The reaction mixture is stirred until the reaction is complete as determined by thin layer chromatography. Water is added to the reaction until the color is dissipated. The reaction mixture is extracted with ethyl acetate, washed with water, and concentrated to a residue. A yield of 92% for the product is shown by chromatography.

Workup

temperatureis maintained at -40° C
temperatureis maintained at -40° C
stirringThe reaction mixture is stirred until the reaction
extractionThe reaction mixture is extracted with ethyl acetate
washwashed with water
concentrationconcentrated to a residue

Sources & evidence

ORD record: ord-87fac8ba9bb44990afdb80cc3b5fb68c
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04659716

Linked notes

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