ChemicalBook CAS DataBase List 3-Ethynylaniline

3-Ethynylaniline synthesis

9synthesis methods

Product Name:3-Ethynylaniline
CAS Number:54060-30-9
Molecular formula:C8H7N
Molecular Weight:117.15

Starting with m-nitrocinnamic acid: First, it undergoes an addition reaction with liquid bromine in glacial acetic acid to generate 3-(3-nitro)phenyl-2,3-dibromopropionic acid; subsequently, it undergoes dehydrobromination and decarboxylation reactions under the action of an organic base (such as DBU) to generate the key intermediate m-nitrophenylacetylene; finally, the nitro group is reduced to an amino group using iron powder in an acidic aqueous ethanol solution to obtain the target product 3-Ethynylaniline.

69088-96-6
111 suppliers
$46.00/250mg

54060-30-9
528 suppliers
$8.00/5g

Yield:54060-30-9 100%

Reaction Conditions:

with sodium hydroxide in toluene at 105 - 110; for 4 h;Inert atmosphere;

Steps:

7

Example 7 - Synthesis of 3-ethynylanyline of formula (IV-a); - exemplifying the invention. Synthesis scheme [Show Image] Literature reference: US 2006/0188498 In a 500 ml flask provided with a thermometer, Dean-Stark apparatus and a drip funnel there are introduced - in succession at 25°C and under nitrogen atmosphere - 30 g of 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol of formula (IV), 2.2 g of caustic soda and 240 mL of Toluene. The mixture is heated to the reflux temperature (105-110°C) for 4 hrs, collecting the distillate in the Dean-Stark apparatus. Fresh toluene is simultaneously added to the reaction mixture so as to maintain a minimum volume of 180 ml (6 vol) within the flask. This allows removing acetone from the reaction mixture. After the 4 hours, it is stirred at reflux until the reaction is completed, controlling the trend thereof by means of TLC. Upon completion of the reaction it is cooled to 25 °C and a mixture made up of 20 mL of Toluene and 250 mg of dicalite is added. The reaction mixture is stirred for 15 min. The reaction mixture is filtered and the solid is washed using 15 mL of Toluene. The filtrates are combined and the resulting solution is concentrated at 40°C under vacuum up to residue. The product is obtained as oil (20.7 g) with quantitative yield.

References:

EP2433931,2012,A1 Location in patent:Page/Page column 10

3034-94-4 Synthesis

3034-94-4
145 suppliers
$9.00/250mg

54060-30-9
528 suppliers
$8.00/5g

References

70933-58-3 Synthesis

70933-58-3
54 suppliers
$45.00/50mg

54060-30-9
528 suppliers
$8.00/5g

References

69088-96-6
111 suppliers
$46.00/250mg

54060-30-9
528 suppliers
$8.00/5g

31661-59-3 Synthesis

31661-59-3
58 suppliers
inquiry

References

110598-30-6
45 suppliers
$41.00/100mg

54060-30-9
528 suppliers
$8.00/5g

References

3-Ethynylaniline Related Search:

N,N-Dimethylaniline Phenylacetylene p-Anisidine Methyl anthranilate Aniline 2-BENZOYLACETANILIDE 4-Aminobenzoic acid Diphenylamine Metanilic acid Sulfanilamide