Trimethyl orthoformate → 5-nitro-2-(1H-tetrazol-1-yl)pyridine

HRID 1039063Notes

Reaction equation

HRID 1039063 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].[N-:11]=[N+:12]=[N-:13].[Na+].[CH3:15]OC(OC)OC>C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:15]=[N:13][N:12]=[N:11]2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 33557Sodium AzideHCID 778882-Amino-5-nitropyridine

Product 1

HCID 669272915-nitro-2-(1H-tetrazol-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was synthesized using 5-nitropyridin-2-amine (1 g, 6.97 mmol), sodium azide (0.68 g, 10.5 mmol), trimethylorthoformate (1.2 g, 11.2 mmol) and acetic acid (14 mL) and stirred at room temperature over night. The reaction was heated to 120° C. reflux for 7 hours. The reaction was cooled down to room temperature, concentrated to take off acetic acid. Ice water (50 mL) was added, extracted with ethyl acetate (50 mL), second wash with sodium hydroxide (1N, 20 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 50 gram Biotage SNAP KP-Sil™ silica gel cartridge eluting with 30% ethyl acetate/hexanes to give the title compound as a pale yellow solid.

Workup

  1. customThe title compound was synthesized
  2. temperatureThe reaction was heated to 120° C.
  3. temperaturereflux for 7 hours
  4. temperatureThe reaction was cooled down to room temperature
  5. concentrationconcentrated
  6. additionIce water (50 mL) was added
  7. extractionextracted with ethyl acetate (50 mL)
  8. washsecond wash with sodium hydroxide (1N, 20 mL)
  9. dry with materialThe organic phase was dried by magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. custompurified by column chromatography through a 50 gram Biotage SNAP KP-Sil™ silica gel cartridge
  13. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-641529f8d9dc4f24853955181d9c5f50
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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