Nitric Acid → HCID 89726433, compound

HRID 1777765Notes

Reaction equation

HRID 1777765 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.[C:13]([O:16]C(=O)C)(=O)[CH3:14].[N+:20]([O-])([OH:22])=[O:21]>>[N+:20]([C:3]1[CH:4]=[C:5]([N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)[CH:6]=[CH:7][C:2]=1[NH:1][C:13](=[O:16])[CH3:14])([O-:22])=[O:21]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 7358264-(1,2,4-Triazol-1-yl)aniline

Product 1

HCID 89726433HCID 89726433, compound

Conditions

Temperature
10 °C

Procedure

1-(4′-Aminophenyl)-1,2,4-triazole (500 mg) was added to acetic anhydride (2.3 mL) over 10 min and the mixture was cooled down to 10° C. HNO3 (65% in water, 0.65 mL) was added slowly to keep the temperature of the reaction mixture below 15° C. After the end of the addition, the reaction mixture was allowed to warm to RT over 1 h, was quenched with ice-cold water and stirred for 10 min. The resulting mixture was basified with aq. NH4OH (25%) to pH=12 and extracted with DCM. The phases were separated and the org. phase was evaporated in vacuo. The residue was taken up in H2SO4 (2 mL), the resulting solution was cooled down to 0° C. and HNO3 ((65% in water, 0.3 mL) was added. The mixture was stirred at 0° C. for 30 min and poured onto ice. After 10 min stirring, aq. NH4OH (25%) was added until pH=2 and the mixture was extracted with DCM. The org. layer was evaporated in vacuo to afford 130 mg of orange solid. LC-MS (B): tR=0.61 min; [M+H]+: 248.09.

Workup

  1. customthe temperature of the reaction mixture below 15° C
  2. additionAfter the end of the addition
  3. temperatureto warm to RT over 1 h
  4. customwas quenched with ice-cold water
  5. extractionextracted with DCM
  6. customThe phases were separated
  7. customphase was evaporated in vacuo
  8. temperaturethe resulting solution was cooled down to 0° C.
  9. additionHNO3 ((65% in water, 0.3 mL) was added
  10. stirringThe mixture was stirred at 0° C. for 30 min
  11. additionpoured onto ice
  12. stirringAfter 10 min stirring
  13. additionaq. NH4OH (25%) was added until pH=2
  14. extractionthe mixture was extracted with DCM
  15. customlayer was evaporated in vacuo

Sources & evidence

ORD record
ord-fdb697a22080488d80e09cd5d8d64495
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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