Trimethyl orthoformate → methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate

HRID 714290Notes

Reaction equation

HRID 714290 reaction equation
[NH:1]([C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][N:14]=1)C([O-])=O)=[O:4])[NH2:2].[CH:15]([O:20]C)([O:18][CH3:19])OC.O.[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[O:4]=[C:3]1[NH:1][N:2]=[CH:23][N:5]1[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][N:14]=1)[C:15]([O:18][CH3:19])=[O:20]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 866530522-(Hydrazinecarboxamido)isonicotinate

Product 1

HCID 58247755methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinateYield 207.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(hydrazinecarboxamido)isonicotinate (2.10 g, 10.0 mmol) in ethanol (140 mL) was added trimethyl orthoformate (2.43 g, 22.9 mmol) and p-toluenesulfonic acid monohydrate (0.70 g, 3.68 mmol) at ambient temperature. The reaction mixture was refluxed for 4 hours, cooled to ambient temperature and concentrated in vacuo to a minimum amount of volume. The solid was filtered, washed with cold methanol (20 mL) and dried in vacuo to give methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate as a colorless solid (1.68 g, 76%): MS (ES+) m/z 221.1 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. concentrationconcentrated in vacuo to a minimum amount of volume
  3. filtrationThe solid was filtered
  4. washwashed with cold methanol (20 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-15afd3a8d49945b6af344f4788bf7d36
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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