ChemicalBook CAS DataBase List Mordant Orange 1

Mordant Orange 1 synthesis

8synthesis methods

Product Name:Mordant Orange 1
CAS Number:2243-76-7
Molecular formula:C13H9N3O5
Molecular Weight:287.23

4-Nitrobenzenamine diazotization, and 2-Hydroxybenzoic acid?coupling.

54-21-7 Synthesis

54-21-7
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2243-76-7
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Yield: 60%

Reaction Conditions:

Stage #1:4-nitro-aniline with hydrogenchloride;sodium nitrite in water at 0 - 5; for 0.75 h;
Stage #2:sodium salicylate in water at 0 - 5; for 2 h;Alkaline conditions;

Steps:

General procedure: Synthetic procedures. Aromatic amine (1a-i) (0.01 mol) was dissolved in 1:1 ratio of conc. HCl and water. Sodium nitrite solution (0.02 mol/mL) was added to the reaction mixture dropwise with continuous stirring. The reaction mixture was stirred for 45 min. at a temperature of 0-5 oC. The diazotization step was followed by coupling of the diazotized amines by drop wise addition to the solution of sodium salicylate (0.01 mole of salicylic acid dissolved in 0.02 mol/mL solution of sodium hydroxide). The reaction was stirred at 0-5 oC for 2 hours under alkaline conditions. The conjugates of salicylic acid and aromatic amines (3a-i) were obtained as orange to red powders after the pH was neutralized to 6-7.

References:

Harveer, Kaur;Jasmeen, Sidana [Bulletin of the Chemical Society of Ethiopia,2014,vol. 28,# 3,p. 475 - 480]

100-01-6
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69-72-7 Synthesis