Hydrochloric Acid → HCID 23364615, compound

HRID 259897

Reaction equation

HRID 259897 reaction equation
[N:1]([O-])=O.[Na+].[N+:5]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([NH2:18])=[CH:10][CH:9]=1)([O-:7])=[O:6].[ClH:19]>O.CC(O)=O>[ClH:19].[NH:18]([C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([N+:5]([O-:7])=[O:6])=[CH:9][CH:10]=1)[NH2:1]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid3×HCID 130574-Nitro-1-naphthylamineHCID 23668193Sodium Nitrite

Product 1

HCID 23364615HCID 23364615, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of 1.9 g of sodium nitrite in 10 ml of water is added to a suspension, cooled to -5° C., of 5.2 g of 4-nitro-1-naphthylamine in 150 ml of concentrated HCl, 100 ml of 1N HCl and 150 ml of AcOH. The mixture is left stirring for 1 hour 15 minutes at a temperature of between -5° C. and 0° C. It is cooled to -15° C., and a solution of 12.5 g of stannous chloride dihydrate in 30 ml of concentrated HCl is added very slowly. The temperature is allowed to rise to RT and the reaction mixture is kept stirring for 2 hours 30 minutes. It is filtered, the solid is then taken up with water and the mixture is filtered again. 5.9 g of the expected product are obtained.

Workup

  1. waitThe mixture is left
  2. customto rise to RT
  3. stirringthe reaction mixture is kept stirring for 2 hours 30 minutes
  4. filtrationIt is filtered
  5. filtrationthe mixture is filtered again

Sources & evidence

ORD record
ord-3b53c12f67ef441a90600ff8c11b25f0
Source dataset
uspto-grants-1996_06
Patent number
US05523455

Linked notes

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