C(N(CC)CC)C.[Cl-].[CH2:9]([NH:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1I)[CH:10]=[CH2:11]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:11][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:21])[NH:12][CH:9]=1Under an N2 atmosphere, 985 ml (7.07 mol) of triethylamine, 892 g (3.21 mol) of tetra-nbutylammonium chloride and 12.77 g (57 mmol) of Pd(OAc)2 are added to 815 g (2.8 mol) of 2-iodo-benzoic acid allylamide in 4.5 l of DMF, and heated to 100° C. After 4 h, cooling is effected to RT, and the mixture is partially concentrated by evaporation on a RE. The residue is partitioned between 5 l of water and 5 l of EtOAc, the water phase is separated and extracted twice with EtOAc. The organic phases are washed with water, 0.1 N HCl, water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2, EtOAc/toluene 1:1) and crystallisation from toluene yields 4-methyl-2H-isoquinolin-1-one; m.p. 175-176° C.
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