4-Chloroaniline → Benzenediazonium, 4-chloro-, chloride

HRID 654299Notes

Reaction equation

HRID 654299 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]([O-])=O.[Na+]>O.Cl>[Cl-:1].[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([N+:6]#[N:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 78124-ChloroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 11819533Benzenediazonium, 4-chloro-, chloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 4-chloroaniline (21.14 g, 0.166 mol) in water (156 ml) and 12N HCl (46 ml) at 0° was added sodium nitrite (12.62 g, 0.182 mol) in water (156 ml) over 20 minutes keeping the reaction temperature below 10°. The solution of 4-chlorobenzenediazonium chloride was filtered, kept at 0° for 30 minutes and then used in the next step.

Workup

  1. customthe reaction temperature below 10°
  2. filtrationThe solution of 4-chlorobenzenediazonium chloride was filtered

Sources & evidence

ORD record
ord-70947aa2713d450dac14bddce843d449
Source dataset
uspto-grants-1992_07
Patent number
US05130462

Reaction notes

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