3-Nitro-1,2-phenylenediamine → HCID 178526563, compound

HRID 1516431Notes

Reaction equation

HRID 1516431 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:11])([O-:3])=[O:2].[N:12]([O-])=O.[Na+]>CC(O)=O>[N+:1]([C:4]1[C:5]2[N:11]=[N:12][NH:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 43595253-Nitro-1,2-phenylenediamineHCID 23668193Sodium Nitrite

Product 1

HCID 178526563HCID 178526563, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 3-nitrobenzene-1,2-diamine (15.0 g) in AcOH (100 mL) was added NaNO2 (7.0 g). The reaction mixture was stirred for 15 min at RT, then heated at 60° C. for about 2 h, over which time the reaction mixture turned red. The mixture was cooled to RT, diluted with ice water, and the resulting precipitate filtered off and washed with ice water, then dried under vacuum to yield 4-nitro-1H-benzotriazole (13.45 g, 83.6% yield) as a light brown solid. The product was used without further purification.

Workup

  1. temperatureheated at 60° C. for about 2 h, over which time the reaction mixture
  2. temperatureThe mixture was cooled to RT
  3. filtrationthe resulting precipitate filtered off
  4. washwashed with ice water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-635e645ab46e4232bdf052e2dc19ab61
Source dataset
uspto-grants-2012_07
Patent number
US08227478B2

Reaction notes

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