Hydrochloric Acid → 1H-Benzotriazole, 1-methyl-5-nitro-

HRID 416269Notes

Reaction equation

HRID 416269 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([NH2:12])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1.Cl.[N:14]([O-])=O.[Na+].[OH-].[K+]>O>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[N:12]=[N:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 34200251-N-methyl-4-nitrobenzene-1,2-diamineHCID 23668193Sodium Nitrite

Product 1

HCID 3352691H-Benzotriazole, 1-methyl-5-nitro-Yield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A stirred suspension of diamine 248 (1.13 g, 6.76 mmol) and concentrated HCl (5.6 mL, 67 mmol) in water (22 mL) at 0° C., was treated with a solution of NaNO2 (586 mg, 8.5 mmol) in water (10 mL). The mixture was stirred at the same conditions for 3 h, warmed to room temperature, neutralized with a 5% w/v solution of KOH in water and filtered. The solid was washed with cold water and dried to afford title compound 264 (975 mg, 81% yield). 1H NMR: (DMSO) δ (ppm): 9.00 (d, J=1.3 Hz, 1H), 8.39 (dd, J=1.3, 8.8 Hz, 1H), 8.09 (d, J=8.8 Hz, 1H), 4.40 (s, 3H).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with cold water
  3. customdried

Sources & evidence

ORD record
ord-747ef4de3ce547649ea92c2de1c140bc
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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