2H-Pyran-2-one,4-amino-6-methyl-(9CI)

Base Information

• Chemical Name: 2H-Pyran-2-one,4-amino-6-methyl-(9CI)
• CAS No.: 132559-90-1
• Molecular Formula: C6H7NO2
• Molecular Weight: 125.13
• Mol file: 132559-90-1.mol

Synonyms:2H-Pyran-2-one,4-amino-6-methyl-(9CI)

Chemical Property of 2H-Pyran-2-one,4-amino-6-methyl-(9CI)

Chemical Property:

• Boiling Point: 227.9±29.0 °C(Predicted)
• PKA: 2.28±0.20(Predicted)
• PSA: 56.23000
• Density: 1.201±0.06 g/cm3(Predicted)
• LogP: 1.11160

Purity/Quality:

97% ^*data from raw suppliers

4-Amino-6-Methyl-2H-Pyran-2-One ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 4-Amino-6-methyl-2H-pyran-2-one is a key intermediate in the synthesis of bis(4-amino-6-methyl-2-oxo-2H-pyran-3-yl)arylmethanes, formed through the condensation of 2H-Pyran-2-one,4-amino-6-methyl-(9CI) with aromatic aldehydes under acid catalysis. It serves as a versatile precursor, enabling the introduction of amino functionality at the C-4 position of the pyran-2-one ring, which is crucial for further derivatization. 2H-Pyran-2-one,4-amino-6-methyl-(9CI)'s reactivity with aldehydes highlights its utility in constructing more complex heterocyclic systems.

Technology Process of 2H-Pyran-2-one,4-amino-6-methyl-(9CI)

There total 4 articles about 2H-Pyran-2-one,4-amino-6-methyl-(9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-azido-6-methyl-2H-oxopyran-2-one (132559-92-3) → 4-amino-6-methyl-2H-pyran-2-one (132559-90-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90086-9

Reference yield:

4-hydroxy-6-methyl-2-pyron (675-10-5) → 4-amino-6-methyl-2H-pyran-2-one (132559-90-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / phosphorous tribromide / diethyl ether; dimethylformamide / 20 h / 60 °C

2: 83 percent / sodium azide / dimethylformamide / 1 h / Ambient temperature

3: 100 percent / hydrogen / 10percent Pd/C / ethanol / 1 h / Ambient temperature

With sodium azide; hydrogen; phosphorus tribromide; palladium on activated charcoal; In diethyl ether; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90086-9

Reference yield:

4-chloro-6-methyl-2H-pyran-2-one (17422-72-9) → 4-amino-6-methyl-2H-pyran-2-one (132559-90-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / sodium azide / dimethylformamide / Ambient temperature

2: 100 percent / hydrogen / 10percent Pd/C / ethanol / 1 h / Ambient temperature

With sodium azide; hydrogen; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90086-9

upstream raw materials:

4-azido-6-methyl-2H-oxopyran-2-one

4-hydroxy-6-methyl-2-pyron

4-chloro-6-methyl-2H-pyran-2-one

4-bromo-6-methyl-2H-pyran-2-one

Downstream raw materials:

bis(4-amino-6-methyl-2-oxo-2H-pyran-3-yl)(3-nitrophenyl)methane

bis(4-amino-6-methyl-2-oxo-2H-pyran-3-yl)(2-nitrophenyl)methane

bis(4-amino-6-methyl-2-oxo-2H-pyran-3-yl)(4-chlorophenyl)methane

Refernces

4-AMINO-6-METHYL-2H-PYRAN-2-ONE. PREPARATION AND REACTIONS WITH AROMATIC ALDEHYDES.

10.1016/S0040-4020(01)90086-9

The research focuses on the synthesis of bis(4-amino-6-methyl-2-oxo-2H-pyran-3-yl)arylmethanes (1). The key starting material is 4-amino-6-methyl-2H-pyran-2-one (10), which is synthesized from 4-hydroxy-6-methyl-2H-pyran-2-one (2) through a series of reactions. The researchers initially attempted to synthesize the target compounds by reacting arylbis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methanes (2) with ammonia, but this led to the formation of arylbis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methanes (4) instead. To overcome this, they explored the use of a good leaving group at the C-4 position and eventually found that using 4-amino-6-methyl-2H-pyran-2-one (10) as a starting material was a feasible alternative. The synthesis involved condensation of 10 with various aromatic aldehydes under catalysis by p-toluenesulfonic acid in toluene, yielding the desired bis(4-amino-6-methyl-2-oxo-2H-pyran-3-yl)arylmethanes (1). The study also involved the synthesis of several intermediate compounds, such as 4-azido-6-methyl-2H-pyran-2-one (12) and 1-(6-methyl-2-oxo-2H-pyran-4-yl)imidazole (14), using different reagents and conditions. The compounds were characterized by spectroscopic and analytical data, providing insights into their structures and properties.

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