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

HRID 1852419Notes

Reaction equation

HRID 1852419 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

4

Reactant 3

HCID 6342AcetonitrileHCID 57418452Ammonium cerium-nitrateHCID 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%).

Workup

  1. concentrationconcentrated at reduced pressure
  2. custompartitioned between EtOAc and water
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was purified by silica column chromatography (EtOAc)

Sources & evidence

ORD record
ord-9feef2b7443c41928791cc9abcc96372
Source dataset
uspto-grants-2015_02
Patent number
US08962598B2

Reaction notes

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