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

HRID 1853375

Reaktionsgleichung

Reaktionsgleichung von HRID 1853375
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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-db0a41d75a3b433dbf0fb0ee56502b9c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962638B2

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