ChemicalBook CAS DataBase List 2-Azabicyclo[2.2.1]hept-5-en-3-one

2-Azabicyclo[2.2.1]hept-5-en-3-one synthesis

8synthesis methods

Product Name:2-Azabicyclo[2.2.1]hept-5-en-3-one
CAS Number:49805-30-3
Molecular formula:C6H7NO
Molecular Weight:109.13

542-92-7

506-77-4

49805-30-3

In a 1000 mL reaction flask equipped with a thermometer and an off-gas absorption device, 500 mL of methanol, 50 g of cross-linked polystyrene-sulfinyl and 5.0 g of cyclopentadiene were added. The reaction system was cooled to 0-5°C and 2.5 g of cyanogen chloride gas was slowly passed through, while an ethanol solution of 5% sodium hydroxide was added dropwise to maintain the pH of the reaction system between 4-5. After the dropwise addition, the reaction was continued for 8 hours. After completion of the reaction, the solid was separated by filtration. The resulting solid was added to 100 mL of 5% ethanol solution of acetic acid and the reaction was continued for 8 hours at room temperature. Subsequently, the solid catalyst particles were removed by filtration and the filtrate was concentrated to afford the white crystalline product 2-azabicyclo[2.2.1]hept-5-en-3-one in a yield of 4.21 g in 95% yield (as cyanogen chloride) and 99.5% purity.

542-92-7
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506-77-4
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49805-30-3
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Yield:49805-30-3 95%

Reaction Conditions:

with sodium hydroxide in methanol at 0 - 5; pH=4 - 5; for 8 h;Diels-Alder Cycloaddition;

Steps:

1 Embodiment 1

In the with of the thermometer and the tail gas absorption device 1000 ml of in [...], adding 500 ml of methanol, 50 g cross-linked polystyrene-sulfinyl and sodium 5.0 g of cyclopentadiene, control low-temperature 0 - 5 °C, slow access 2.5 g cyanogen chloride gas, at the same time dropping 5% of sodium hydroxide in an alcoholic solution, control pH value is 4 - 5 between. The end of the dropping, the reaction to 8 hours. Filtering, separating out the solid.This solid is added to the 100 ml 5% alcoholic solution of acetate, to continue the reaction at room temperature for 8 hours, filtering the solid catalyst particles, the filtrate is concentrated, separating white crystal product, is azabicyclo [2, 2, 1] heptyl -5 - ene -3 - one, the product quality is 4.21 g, yield is 95% (relative to the cyanogen chloride), purity 99.5%.

References:

CN107805217,2018,A Location in patent:Paragraph 0036-0043