Methylamine → 6-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-(methylamino)pyridine-3-carbonitrile

HRID 13802

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[N:3]=1.[NH2:25][CH3:26]>C1COCC1>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[C:4]1[N:3]=[C:2]([NH:25][CH3:26])[C:7]([C:8]#[N:9])=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 67 °C

Procedure

To 2-chloro-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carbonitrile (2.03 g) in THF (14 mL) was added H2NCH3 (13 mL, 2 M solution in THF). The reaction was heated to 67° C. in a closed vessel for 9 hours before concentrating. The product was dissolved in EtOAc and washed with saturated aqueous NaHCO3 solution. The solution was concentrated and purified via flash chromatography on silica gel with a gradient elution of 0% to 10% EtOAc in hexane affording the title compound. HPLC/MS: 387.8(M+1), 389.8 (M+3); Rt=4.26 min.

Workup

concentrationbefore concentrating
dissolutionThe product was dissolved in EtOAc
washwashed with saturated aqueous NaHCO3 solution
concentrationThe solution was concentrated
custompurified via flash chromatography on silica gel with a gradient elution of 0% to 10% EtOAc in hexane affording the title compound

Sources & evidence

ORD record: ord-8388cc3948c24d1aa622a1a5a14c0e04
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728141B2

Linked notes

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