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4-Pyridinemethanol, 2-methoxy-(9CI) is an important intermediate in the synthesis of various pharmaceuticals and agrochemicals.
It finds application in the synthesis of active pharmaceutical ingredients (APIs) for treating diseases such as cancer, inflammatory diseases, and other disorders.
The synthetic routes for 4-Pyridinemethanol, 2-methoxy-(9CI) can be broadly classified into two categories: traditional and contemporary routes.
Traditional Synthetic Routes:
The traditional synthetic routes for 4-Pyridinemethanol, 2-methoxy-(9CI) involved multi-step synthesis, which was time-consuming, expensive, and had a high risk of producing impurities.
The traditional routes involved the use of hazardous reagents and the generation of large amounts of waste.
One of the traditional synthetic routes involved the reduction of 2-methoxy-3-nitroaniline (1) to form 2-methoxy-3-aminopropanamide (2) using a reducing agent such as lithium aluminum hydride (LiAlH4) in the presence of a suitable solvent such as ether or THF.
The amino group was then converted to a methoxy group using a reagent such as dimethyl sulfate (DMS) in the presence of a solvent such as pyridine.
The resulting compound was then condensed with formaldehyde to form 4-Pyridinemethanol, 2-methoxy-(9CI) (3) (Figure 1).
Contemporary Synthetic Routes:
The contemporary synthetic routes for 4-Pyridinemethanol, 2-methoxy-(9CI) are more efficient, cost-effective, and environmentally friendly compared to the traditional routes.
The contemporary routes involve the use of modern synthetic methods such as green chemistry, organic catalysis, and enzymatic reactions.
One of the contemporary synthetic routes involves the synthesis of 2-methoxy-3-aminopropanamide (2) using a greener and more efficient method such as the reaction of 2-methoxy-3-nitroaniline (1) with ammonia in the presence of a catalyst such as palladium on barium oxide (Pd/BaO) and a solvent such as ethanol or methanol.
The resulting compound was then converted to 4-Pyridinemethanol, 2-methoxy-(9CI) (3) using a reagent such as sodium methoxide in the presence of a solvent such as methanol (Figure 2).
Figure 1: Traditional Synthetic Route for 4-Pyridinemethanol, 2-methoxy-(9CI)
Figure 2: Contemporary Synthetic Route for 4-Pyridinemethanol, 2-methoxy-(9CI)
Advantages of Contemporary Synthetic Routes:
The contemporary synthetic routes for 4-Pyridinemethanol, 2-methoxy-(9CI) offer several advantages over the traditional routes, including:
- Reduced time and cost: The contemporary routes involve fewer steps and the use of less expensive reagents and catalysts, resulting in reduced time and cost.
- Reduced waste generation: The contemporary routes involve the use of greener and more efficient reagents and solvents, resulting in reduced waste generation.
- Improved purity: The contemporary routes involve the use of modern synthetic methods such as organic catalysis and enzymatic reactions, resulting in improved purity