Hydrochloric Acid → Benzenediazonium, 2-nitro-, chloride (1:1)

HRID 2296837

Reaction equation

HRID 2296837 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[ClH:11].[N:12]([O-])=O.[Na+]>O>[Cl-:11].[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[N+:6]#[N:12])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69462-NitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 148932Benzenediazonium, 2-nitro-, chloride (1:1)Yield 359.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a 500 mL three-necked flask equipped with a mechanical stirrer are added 60 g of 2-nitroaniline and 134.2 g of concentrated hydrochloric acid. After heating to 65° C., 46 g of water is added after which the reactor is cooled to 0° C. Sodium nitrite (74.2 g, 40% aqueous solution) is slowly added to the slurry while maintaining a temperature of 0° C. The diazonium salt solution is filtered to give 290 g of solution which is stored at −15° C. for later use.

Workup

  1. customTo a 500 mL three-necked flask equipped with a mechanical stirrer
  2. temperatureis cooled to 0° C
  3. temperaturewhile maintaining a temperature of 0° C
  4. filtrationThe diazonium salt solution is filtered

Sources & evidence

ORD record
ord-f6c1892ad259440082a2211342bc8291
Source dataset
uspto-grants-2002_12
Patent number
US06489383B1

Linked notes

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