Potassium Carbonate → Methyl-3-((6-methoxy-3-nitropyridin-2-yl)amino)-2-methylpropanoate

HRID 1485461Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[CH3:13][O:14][C:15](=[O:20])[CH:16]([CH3:19])[CH2:17][NH2:18].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:13][O:14][C:15](=[O:20])[CH:16]([CH3:19])[CH2:17][NH:18][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-chloro-6-methoxy-3-nitropyridine (3 g, 15.91 mmol) in tetrahydrofuran (20 mL) was added methyl-3-amino-2-methylpropanoate (2.05 g, 17.50 mmol) and potassium carbonate (4.40 g, 31.82 mmol). The mixture was stirred at 50° C. for 12 hours. The reaction mixture was concentrated in vacuo and washed with water (20 mL), extracted with acetic ester (20 mL×3). The combined organic phase was dried by anhydrous sodium sulphate, and then filtered. The filtrate was concentrated and purified by column chromatograph silica gel (elute: dichloromethane/Methanol: 100:1→80:1) to give methyl-3-((6-methoxy-3-nitropyridin-2-yl)amino)-2-methylpropanoate (4.2 g, 97%) as a yellow oil.

Workup

concentrationThe reaction mixture was concentrated in vacuo
washwashed with water (20 mL)
extractionextracted with acetic ester (20 mL×3)
dry with materialThe combined organic phase was dried by anhydrous sodium sulphate
filtrationfiltered
concentrationThe filtrate was concentrated
custompurified by column chromatograph silica gel (elute: dichloromethane/Methanol: 100:1→80:1)

Sources & evidence

ORD record: ord-c3dd6a517e164204930206a102c71e5a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422292B2

Reaction notes

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