Diethyl (ethoxymethylene)malonate → Diethyl 2-((6-ethylpyridin-2-ylamino)methylene)malonate

HRID 883847

Reaction equation

HRID 883847 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][CH:4]=1)[CH3:2].[CH2:10]([O:12][C:13](=[O:24])[C:14](=[CH:20]OCC)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:11]>>[CH2:10]([O:12][C:13](=[O:24])[C:14](=[CH:20][NH:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:1][CH3:2])[N:8]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:11]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 890216-Ethylpyridin-2-amine

Product 1

HCID 12354398Diethyl 2-((6-ethylpyridin-2-ylamino)methylene)malonate

Conditions

Temperature
100 °C

Procedure

The crude product from Example 8b was combined with 2-ethoxymethylene-malonic acid diethyl ester (6.6 mL, 0.032 mol) and the mixture heated under a N2 atmosphere in an oil bath at 100° C. for 2 h. Purified by flash chromatography on silica gel eluting with EtOAc/hexane giving the title compound (7.16 g, 98%).

Workup

  1. customPurified by flash chromatography on silica gel eluting with EtOAc/hexane giving the title compound (7.16 g, 98%)

Sources & evidence

ORD record
ord-eb849b1d0bbe4df2b73112607cc62a02
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Linked notes

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