Ammonium cerium-nitrate → HCID 68008654, compound

HRID 533165Notes

Reaction equation

HRID 533165 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N:11][C:12]2[CH2:13][CH2:14][N:15](CC3C=CC(OC)=CC=3)[C:16](=[O:19])[C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[NH4+].[Ce]>CC#N.O>[CH2:1]([O:8][C:9]1[CH:10]=[N:11][C:12]2[CH2:13][CH2:14][NH:15][C:16](=[O:19])[C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 57418452Ammonium cerium-nitrateHCID 68008361HCID 68008361, compound

Product 1

HCID 68008654HCID 68008654, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

3-(Benzyloxy)-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (1.05 g, 2.8 mmol) was dissolved in MeCN (50 mL). To the solution cerium ammonium nitrate (15.4 g, 28 mmol) in water (50 mL) was added slowly at room temperature. The reaction was stirred for 1 h at the same temperature, partitioned between EtOAc (200 mL) and brine (200 mL). The organic layers were dried, concentrated and purified by column chromatography (MeOH, DCM 0-5%). The compound was obtained as an off white solid (293 mg, 41%). 1H NMR (400 MHz, CDCl3) δ 8.44 (d, J=2.8, 1H), 7.94 (d, J=2.8, 1H), 7.47-7.35 (overlapped, 5H), 6.05 (br s, NH), 5.16 (s, 2H), 4.74 (s, 2H), 3.82 (s, 3H), 3.66 (td, J=6.8, 2.4, 2H), 3.17 (td, J=6.8, 2.4, 2H); LC-MS (M+H)=255.1

Workup

  1. custompartitioned between EtOAc (200 mL) and brine (200 mL)
  2. customThe organic layers were dried
  3. concentrationconcentrated
  4. custompurified by column chromatography (MeOH, DCM 0-5%)

Sources & evidence

ORD record
ord-12fd7a79f2dd48ba8395c97402ee7f59
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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