Hydrochloric Acid → HCID 21501418, compound

HRID 1729833Notes

Reaction equation

HRID 1729833 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](N)=[C:4]([Cl:13])[CH:3]=1.[ClH:14].N([O-])=O.[Na+]>O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:14])=[C:4]([Cl:13])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21501427HCID 21501427, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21501418HCID 21501418, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To an ice-cooled solution of 4-bromo-2-chloro-1-naphthylamine (25.7 g) in water (60 ml) and concd. hydrochloric acid (30 ml) was added a solution of sodium nitrite (8.4 g) in water (16 ml) at 0°-5° C. The diazonium solution was stirred at same temperature an hour. There was added to it an ice-cooled solution of cuprous chloride (11 g) in concd. hydrochloric acid (60 ml). After stirring at 0°-5° C for 2 hrs., the mixture was warmed to room temperature. The brown percipitate was collected, washed with cold water, dried, and crystallized from EtOH to give colorless crystals (14.7 g, 75 %) of mp 84°-86° C.

Workup

  1. customThe brown percipitate was collected
  2. washwashed with cold water
  3. customdried
  4. customcrystallized from EtOH

Sources & evidence

ORD record
ord-d1d0f4d320fc46f7ac6616e8e4bf7c9d
Source dataset
uspto-grants-1976_11
Patent number
US03989746

Reaction notes

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