Potassium ethyl malonate → 3-Oxo-3-(3-[1,2,4]triazol-4-yl-phenyl)-propionic acid ethyl ester

HRID 1745526Notes

Reaction equation

HRID 1745526 reaction equation
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=O)[CH:5]=1.ClC(OCC)=O.CCN(CC)CC.[K+].[C:29]([O:35][CH2:36][CH3:37])(=[O:34])[CH2:30]C([O-])=O.[Mg+2].[Cl-].[Cl-]>CC#N.CCN(CC)CC>[CH2:36]([O:35][C:29](=[O:34])[CH2:30][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([N:4]2[CH:5]=[N:1][N:2]=[CH:3]2)[CH:7]=1)[CH3:37]

Participants

7

Reactant 4

HCID 3446434Potassium ethyl malonateHCID 5360315Magnesium ChlorideHCID 64846843-(4H-1,2,4-triazol-4-yl)benzoic acidHCID 19692316ethyl chloroformate Et3N

Product 1

HCID 695928753-Oxo-3-(3-[1,2,4]triazol-4-yl-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Prepared from 3-[1,2,4]triazol-4-yl-benzoic acid [prepared by reaction of 3-aminobenzoic acid with hydrazine hydrate and triethyl orthoformate in acetic acid at 120° C.] by activation with ethyl chloroformate/Et3N and reaction with ethyl malonate potassium salt with Et3N and MgCl2 in CH3CN according to general procedure H (method a). Obtained as a white solid (5.74 g).

Sources & evidence

ORD record
ord-5bccf720c3b6405b858cf3e7337f2150
Source dataset
uspto-grants-2006_03
Patent number
US07018998B2

Reaction notes

Loading…