Nitric Acid → HCID 178524571, compound

HRID 17777Notes

Reaction equation

HRID 17777 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[N:3]=[N:2]1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[N+:13]([C:6]1[C:5]2[NH:1][N:2]=[N:3][C:4]=2[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178524184HCID 178524184, compound

Product 1

HCID 178524571HCID 178524571, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

1H-Benzotriazole-5-carboxylic acid (1 g, 6 mmol) was dissolved, in conc. sulphuric acid (20 ml) and cooled to 0° C. on an ice bath. Nitric acid (20 ml, excess) was added drop wise to the cooled solution over a period of 20 minutes. Stirring was continued for another 15 minutes at 0° C. and then at 90° C. for 2 hours, by which time TLC (A) indicated the conversion of starting material. The solution was cooled to room temperature and poured over ice to precipitate a white solid. The solid was collected by filtration and washed with copious amounts of water until neutral to afford [21] in 48% yield. Rf (A) 0.53; δH(400 MHz; DMSO-d6) 8.77 (1H, s, BT) 9.01 (1H, s, BT) 13.75 (1H, br s, OH) 16.90 (1H, s, NH); m/z (EI−HR) 208.02288 [(M) calc. for C7H4N4O4 208.02325].

Workup

  1. waitat 90° C. for 2 hours
  2. temperatureThe solution was cooled to room temperature
  3. additionpoured over ice
  4. customto precipitate a white solid
  5. filtrationThe solid was collected by filtration
  6. washwashed with copious amounts of water until neutral

Sources & evidence

ORD record
ord-9512274a9e8e4fada6527d3f4a4a4021
Source dataset
uspto-grants-2010_06
Patent number
US07741102B2

Reaction notes

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