Water → Methyl tetrahydro-3-methyl-5-[2-nitro-5-(2-pyridyloxy)phenyl]-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 2255881Notes

Reaction equation

HRID 2255881 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:23]([O-:25])=[O:24])=[C:6]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:9]2=[O:22])[CH:7]=1.[OH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(Cl)Cl.CO>[CH3:15][N:12]1[C:13](=[O:14])[N:8]([C:6]2[CH:7]=[C:2]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH:3]=[CH:4][C:5]=2[N+:23]([O-:25])=[O:24])[C:9](=[O:22])[N:10]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:11]1=[O:16]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 57274056Methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetateHCID 178516071HCID 178516071, compound

Product 1

HCID 53727640Methyl tetrahydro-3-methyl-5-[2-nitro-5-(2-pyridyloxy)phenyl]-2,4,6-trioxo-s-triazine-1(2H)-acetate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (0.55 g, 1.55 mmol), 2-hydroxypyridine (0.25 g, 2.58 mmol) and potassium carbonate (0.37 g, 2.64 mmol) in N,N-dimethylformamide is stirred at room temperature overnight and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 0.2M sodium hydroxide solution, water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a yellow foam. Column chromatography of the foam using silica gel and a 2% methanol in methylene chloride solution gives the title product as a yellow oil which is identified by NMR spectral analysis.

Workup

  1. extractionThe aqueous mixture is extracted with ethyl acetate
  2. washwashed sequentially with water, 0.2M sodium hydroxide solution, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow foam

Sources & evidence

ORD record
ord-08a8eb10a3ee4e568fdfbc25993502cc
Source dataset
uspto-grants-1997_08
Patent number
US05654256

Reaction notes

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