Acetonitrile → N-phenyl-4-diethylphosphoryloxy-1,2-dihydro-1-methyl-2-oxo-quinoline-3-carboxamide

Reaction equation

COC1C=C(OC)C=CC=1C[N:6]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:7]([C:9]1[C:10](=[O:27])[N:11]([CH3:26])[C:12]2[C:17]([C:18]=1[O:19][P:20]([CH2:24][CH3:25])([CH2:22][CH3:23])=[O:21])=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8].[N+]([O-])([O-])=O.[NH4+].[Ce].CC#N>>[C:28]1([NH:6][C:7]([C:9]2[C:10](=[O:27])[N:11]([CH3:26])[C:12]3[C:17]([C:18]=2[O:19][P:20]([CH2:24][CH3:25])([CH2:22][CH3:23])=[O:21])=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:8])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Reactant 3

HCID 6342Acetonitrile

HCID 57418452Ammonium cerium-nitrate

HCID 86691492N-(2,4-dimethoxybenzyl)-N-phenyl-4-diethylphosphoryloxy-1,2-dihydro-1-methyl-2-oxo-quinoline-3-carboxamide

Product 1

HCID 68186865N-phenyl-4-diethylphosphoryloxy-1,2-dihydro-1-methyl-2-oxo-quinoline-3-carboxamideYield 51.3%

Procedure

N-(2,4-dimethoxybenzyl)-N-phenyl-4-diethylphosphoryloxy-1,2-dihydro-1-methyl-2-oxo-quinoline-3-carboxamide (125 mg, 0.22 mmol) was added to a solution of cerium ammonium nitrate in 95% aq. MeCN (0.50 mmol, 0.1 M, 5.0 mL). The reaction mixture was stirred at room temperature for 1 h, concentrated at reduced pressure, and then partitioned between EtOAc and water. The organic phase was washed with water and brine, dried (Na2SO4), and concentrated at reduced pressure. The residue was purified by silica column chromatography (EtOAc) to give the title compound (45 mg, 49%).