Pyridine → N-(4,6-Dichloropyridin-3-yl)-4-methoxy-3,5-dimethylbenzamide

HRID 1401109Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[CH3:13].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[N:18]=[CH:17][C:16]=1[NH2:22].N1C=CC=CC=1>ClCCl>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[N:18]=[CH:17][C:16]=1[NH:22][C:7](=[O:8])[C:6]1[CH:10]=[C:11]([CH3:12])[C:3]([O:2][CH3:1])=[C:4]([CH3:13])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

With ice cooling, 1.20 g of 4-methoxy-3,5-dimethylbenzoyl chloride, dissolved in 1 ml of dry dichloromethane were initially added dropwise to a solution of 0.82 g of 4,6-dichloropyridin-3-ylamine in 8 ml of dry dichloromethane. A solution of 0.4 ml of absolute pyridine in 1 ml of dry dichloromethane was then added, and the reaction was stirred at 0° C. for 2 h, the product partially precipitating slowly. Approx. 10 ml of 10% strength aqueous sodium bisulfate solution were then added, and the mixture was stirred for five minutes. The aqueous phase was then decanted off and the solid-containing organic phase was concentrated under reduced pressure and freeze-dried. This gave 1.63 g (100%) of the product, which was used for the next step without any further purification.

Workup

customthe product partially precipitating slowly
additionApprox. 10 ml of 10% strength aqueous sodium bisulfate solution were then added
stirringthe mixture was stirred for five minutes
customThe aqueous phase was then decanted off
concentrationthe solid-containing organic phase was concentrated under reduced pressure
customfreeze-dried
customThis gave 1.63 g (100%) of the product, which was used for the next step without any further purification

Sources & evidence

ORD record: ord-4bad3cb828f74c45aabede9fbd7441ad
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907093B2

Reaction notes

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