Ammonium cerium-nitrate → HCID 86691490, compound

HRID 1852417Notes

Reaction equation

HRID 1852417 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:7]([C:9]1[C:10](=[O:37])[N:11]([CH3:36])[C:12]2[C:17]([C:18]=1[O:19][P:20]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21])=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8].[N+]([O-])([O-])=O.[NH4+].[Ce]>CC#N>[C:38]1([NH:6][C:7]([C:9]2[C:10](=[O:37])[N:11]([CH3:36])[C:12]3[C:17]([C:18]=2[O:19][P:20]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:21])=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:8])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 57418452Ammonium cerium-nitrateHCID 86691491HCID 86691491, compound

Product 1

HCID 86691490HCID 86691490, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2,4-dimethoxybenzyl)-N-phenyl-4-dibenzylphosphoryloxy-1,2-dihydro-1-methyl-2-oxo-quinoline-3-carboxamide (116 mg, 0.165 mmol) was added to a solution of cerium ammonium nitrate (CAN, 226 mg, 0.412 mmol, 2.5 eq.) in aq. MeCN (95%, 8.0 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 (heptane-EtOAc, 1:1, then 1:2) to give the title compound (61 mg, 67%).

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 (heptane-EtOAc, 1:1

Sources & evidence

ORD record
ord-69605db27e6847b596ce1475f3f2b2e0
Source dataset
uspto-grants-2015_02
Patent number
US08962598B2

Reaction notes

Loading…