Water → Methyl N-(4-methylpyridin-3-yl)carbamate

HRID 2068995

Reaction equation

HRID 2068995 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH2:14].[C:15](=O)([O:18]C)[O:16][CH3:17].O>O1CCCC1.C(OCC)(=O)C>[CH3:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:18])[O:16][CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 12021Dimethyl CarbonateHCID 1379353-Amino-4-picolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 11672725Methyl N-(4-methylpyridin-3-yl)carbamateYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

At about 0° C., potassium tert-butoxide (47 g, 420 mmol, 3.00 equiv.) was added in several batches to a solution of 4-methylpyridin-3-amine (15 g, 139 mmol, 1.00 equiv.) in tetrahydrofuran (400 mL). After stifling the solution for about 30 minutes, dimethyl carbonate (18.8 g, 209 mmol, 1.50 equiv.) was then added. The solution was stirred at ambient temperature for about 16 hours and then water (100 mL) was added. Following standard extractive workup with ethyl acetate (3×200 mL), the crude product was purified by re-crystallization from ethyl acetate/petroleum ether (1:1) to give the title product as a pale yellow solid (17 g; yield=74%). LC-MS: m/z=167 (M+H)+.

Workup

  1. customfor about 30 minutes
  2. customthe crude product was purified by re-crystallization from ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record
ord-6d0f64aa9ba24df1866ac5b506cb324e
Source dataset
uspto-grants-2012_10
Patent number
US08299084B2

Linked notes

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