4-Amino-1-naphthalenecarbonitrile → 4-Cyano-1-hydrazinonaphthalene

HRID 1081441Notes

Reaction equation

HRID 1081441 reaction equation
[N:1]([O-])=O.[Na+].[C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH2:17])=[CH:9][CH:8]=1)#[N:6]>O.Cl>[C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH:17][NH2:1])=[CH:9][CH:8]=1)#[N:6]

Participants

5

Reactant 2

HCID 428284-Amino-1-naphthalenecarbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 221204294-Cyano-1-hydrazinonaphthalene

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4.09 g of sodium nitrite in 30 ml of water is added to a solution, cooled to 0° C., of 8.35 g of 4-cyano-1-naphthylamine in 180 ml of 1N HCl. The mixture is left stirring for 1 hour 15 minutes at 0° C. It is cooled to -10° C., and a solution of 41.75 g of stannous chloride dihydrate in 42 ml of concentrated HCl is added slowly. The reaction mixture is stirred for 1 hour, allowing the temperature to rise to RT. It is filtered. The residue is suspended in water and 20 ml of concentrated NaOH are added. The expected product is obtained after filtration, rinses with water and then drying under vacuum, m=8.6 g.

Workup

  1. waitThe mixture is left
  2. temperatureIt is cooled to -10° C.
  3. stirringThe reaction mixture is stirred for 1 hour
  4. customto rise to RT
  5. filtrationIt is filtered
  6. addition20 ml of concentrated NaOH are added

Sources & evidence

ORD record
ord-5bbabca4274e45d393b2775e29cf9e50
Source dataset
uspto-grants-1996_12
Patent number
US05585497

Reaction notes

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