1006464-30-7 | 5-{[(1,5-dimethyl-1H-pyrazol-4-yl)amino]methyl}-2-methoxyphenol

Availability
Typically In Stock

Description

• Catalog Number: BA53099
• Chemical Name: 5-{[(1,5-dimethyl-1H-pyrazol-4-yl)amino]methyl}-2-methoxyphenol
• CAS Number: 1006464-30-7
• Molecular Formula: C13H17N3O2
• Molecular Weight: 247.2930
• SMILES: CC1=C(C=NN1C)NCC2=CC(=C(C=C2)OC)O

Upstream Synthesis Route

The synthesis of 5-{[(1,5-dimethyl-1H-pyrazol-4-yl)amino]methyl}-2-methoxyphenol can be achieved through a series of steps involving the functionalization of suitable starting materials. Here's a potential synthetic route:

1. **Preparation of 5-Hydroxy-2-methoxybenzaldehyde**: Start with 2-methoxyphenol (also known as guaiacol) and convert it to its corresponding aldehyde, 5-hydroxy-2-methoxybenzaldehyde. This can be accomplished through oxidation using a suitable oxidizing agent, such as Jones reagent (chromium trioxide in aqueous sulfuric acid) or potassium permanganate (KMnO4).

2. **Formation of the Pyrazolylamine Intermediate**: Synthesize the 1,5-dimethyl-1H-pyrazol-4-amine intermediate by reacting 1,5-dimethyl-1H-pyrazole-4-carboxaldehyde with hydroxylamine hydrochloride under suitable conditions. This reaction should yield the corresponding oxime, which can be further reduced to the desired amine using a reducing agent like sodium cyanoborohydride.

3. **Condensation Reaction**: Condense the 1,5-dimethyl-1H-pyrazol-4-amine with the previously prepared 5-hydroxy-2-methoxybenzaldehyde to form the desired product, 5-{[(1,5-dimethyl-1H-pyrazol-4-yl)amino]methyl}-2-methoxyphenol. This condensation reaction can be carried out under suitable conditions, such as refluxing in an appropriate solvent with a catalyst like p-toluenesulfonic acid.

4. **Purification and Isolation**: Purify the crude product obtained from the reaction using techniques such as column chromatography or recrystallization to obtain pure 5-{[(1,5-dimethyl-1H-pyrazol-4-yl)amino]methyl}-2-methoxyphenol.

As with any organic synthesis, the actual steps and conditions may vary depending on the specific starting materials and desired product. Optimization of reaction conditions and purification methods may be necessary to achieve high yields and purity. Additionally, safety precautions should be followed when handling reactive chemicals and conducting chemical reactions.