Ethyl 2,4-dichloro-6-methylnicotinate → Ethyl 2-chloro-4-ethoxy-6-methylpyridine-3-carboxylate

HRID 1508249Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10](Cl)=[CH:9][C:8]([CH3:12])=[N:7][C:6]=1[Cl:13])[CH3:2].[CH3:15][CH2:16][O-:17].[Na+]>CCO.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([O:17][CH2:16][CH3:15])=[CH:9][C:8]([CH3:12])=[N:7][C:6]=1[Cl:13])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2,4-dichloro-6-methylnicotinic acid ethyl ester (2.49 mmol) in 6 mL EtOH was added NaOEt (2.61 mmol). The reaction mixture was heated to 60° C. overnight in a closed vessel. At RT, the mixture was diluted with EtOAc and washed with aq. NH4Cl solution. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification by (KP-SIL™ from Biotage) using Hept/EtOAc (1/1) gives the desired product as beige solid;

Workup

washwashed with aq. NH4Cl solution
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customPurification by (KP-SIL™ from Biotage)

Sources & evidence

ORD record: ord-b25d07b22dc44781a3e68e7e362cec51
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221832B2

Reaction notes

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