Hydrochloric Acid → HCID 21501406, compound

HRID 1729832Notes

Reaction equation

HRID 1729832 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]([CH3:13])[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]([CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 2632244-bromo-2-methylnaphthalen-1-amineHCID 23668193Sodium Nitrite

Product 1

HCID 21501406HCID 21501406, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 4-bromo-2-methyl-1-naphthlamine (10 g) in a mixture of concd. hydrochloric acid (14 ml) and water (14 ml) was added dropwise a solution sodium nitrite (2.8 g) in water (7 ml) at -5°-0° C. The diazonium solution was stirred at 0°-5° C an hour. There was added to it an ice-cooled solution of cuprous chloride (4.4 g) in concd. hydrochloric acid (25 ml). The mixture was stirred at 60° C an hour, and the precipitate was extracted with ether and dried. After evaporating the solvent, the residue was distilled to give a colorless oil(5.4 g, 58 %), bp11 127°-132° C.

Workup

  1. extractionthe precipitate was extracted with ether
  2. customdried
  3. customAfter evaporating the solvent
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-efcc17c2fe104093b57438f0fc5d9aaf
Source dataset
uspto-grants-1976_11
Patent number
US03989746

Reaction notes

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