Hydrochloric Acid → Benzenediazonium, 4-chloro-2-nitro-, chloride

HRID 392556Notes

Reaction equation

HRID 392556 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[N:13]([O-])=O.[Na+]>O>[Cl-:2].[Cl:2][C:3]1[CH:9]=[CH:8][C:6]([N+:7]#[N:13])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69794-Chloro-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 10420991Benzenediazonium, 4-chloro-2-nitro-, chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a 500 mL three-necked flask fitted with a mechanical stirrer are added 134.2 g of concentrated hydrochloric acid and 60 g of 4-chloro-2-nitroaniline. After heating to 65° C., 106.6 g of water is added at which time the temperature is reduced to 0° C. Sodium nitrite (63.4 g, 40 wt %) is slowly added to the slurry while maintaining the solution at 0° C. The diazonium salt solution (281 g) is then filtered and stored at −15° C. until later use.

Workup

  1. customTo a 500 mL three-necked flask fitted with a mechanical stirrer
  2. customis reduced to 0° C
  3. temperaturewhile maintaining the solution at 0° C
  4. filtrationThe diazonium salt solution (281 g) is then filtered
  5. customstored at −15° C. until later use

Sources & evidence

ORD record
ord-3e64c18b98134453bdf47abceefef8a8
Source dataset
uspto-grants-2004_10
Patent number
US06800676B2

Reaction notes

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