HCID 15783546, compound → HCID 59139883, compound

HRID 1624890Notes

Reaction equation

HRID 1624890 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15](=[O:16])[NH:14][C:13](=[O:17])[C:12](C(O)=O)=[N:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]>C1(OC2C=CC=CC=2)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15](=[O:16])[NH:14][C:13](=[O:17])[CH:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 15783546HCID 15783546, compound

Product 1

HCID 59139883HCID 59139883, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 2-(3-nitrophenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (3 g) in diphenylether (30 mL) was refluxed for 1 hour and cooled to room temperature. The mixture was quenched with 1M NaOH solution. The basic aqueous layer was then acidified and extracted with ethyl acetate (×3). The organic layers were successively washed with brine, dried over MgSO4, filtered and concentrated. 1 g (40% yield) of 2-(3-nitrophenyl)-1,2,4-triazine-3,5(2H,4H)-dione 9(C) was recovered and used in next step without any further purification.

Workup

  1. customThe mixture was quenched with 1M NaOH solution
  2. extractionextracted with ethyl acetate (×3)
  3. washThe organic layers were successively washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3d5a29bb50af4788931d2544cd4054c6
Source dataset
uspto-grants-2014_07
Patent number
US08779129B2

Reaction notes

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