SU401666A1 - Method for producing 2-aryl-derivatives of 2-aryl-4,7-dihydro (or 4,5,6,7-tetrahydro) -isoindol - Google Patents

Description

one

The invention relates to a method for producing new compounds that have potential physiological activity and can be used as intermediates in the synthesis of biologically active substances.

The proposed method is based on a known method for producing aromatic aldehydes by reacting an aromatic compound with phosphorus oxychloride in dimethylformamide medium.

The method of producing formyl derivatives of 2-aryl-4,7-dihydro (or 4,5,6,7-tetrahydro) isoindole is that 2 aryl-4,7 dihydro (or 4,5,6,7-tetrahydro) isoindole subject to interaction: tviyu with phosphorus oxychloride in dimethylformamide during cooling, followed by separation of the target product in a known manner.

The process should be carried out at (+5) - (--10) ° C.

Example 1. 1-Formyl-2-phenyl-4,7-dihydroisoindole.

0.025 mol of 2-phenyl-4,7-dihydro-isonndol in 150 ml of freshly distilled dimethylformamide is cooled for 30 min with ice-salt mixture, then 0.025 mol of freshly distilled phosphorus chloride is added dropwise with stirring, maintaining the reaction temperature O-5 ° C. The solution darkens.

The mixture is gradually heated to room temperature, the mixture is boiled for 2 hours in a water bath, cooled to 50 g of crushed ice, and with good stirring, the hydrochloric acid released during the decomposition of phosphorus oxychloride is neutralized with sodium bicarbonate. When standing cold, an oil falls, which is extracted with ether. The ether extract is washed with water and dried with calcined magnesium sulphate. After removal of the solvent, the residue is distilled in vacuo. Yield 52%, kp. 192-195 C / 1 mm Hg. Art.

Found,%: C 80.68, 81.22; H 5.95, 5.63; N 5.86, 5.90.

CisHisNO.

Calculated,%: C 80.78; H 5.88; N 6.28.

Semikarbazon, so pl. 177--179 ° C.

Similarly receive;

5-Methyl-1 (or 3) formyl-2-phenyl-4,7-dihydroisoindole, starting from 0.025 mol of 5-methyl2-feiyl-4, 7-digg} 1droisoindole, 150 ml of dimethylformamide and 0.025 mol of phosphorus oxy56%, t bales 190-193 ° C / 1 mm

Output

handicap, rt. Art.

about/,

p 80.53, 80.46; H 6.48, 6.62;

Found N / 6.06, 5.70.

CieHisNO.

Calculated,%: C, 80.98; H 6.38; N 5.90.

Semikarbazon, so pl. 166-167 ° C.

5-Methyl-1 (or 3) -formyl-2-phenyl-4,5,6,7 tetrahydroisoindole, starting from 0.025 mol 5-Methyl-2-fe11Il-4,5,6,7 - tetrahydroisoipdol, 150 ml of dimethylformamide and 0.025 mol of phosphorus oxychloride. Yield 58%, kp. 165-160 ° C / 1 mm Hg Art.

Found,%; C 79.98, 79.80; H 7.10, 7.07; N 5.87, 6.07.

Ci6H, 7NO.

Calculated,%: C, 80.30; H 7.16; N 5.85.

Semnarbazon, t, il. 160.5-161.5 ° C.

Example 2. 1-Formyl-2-phenyl-4,5,6,7-tetrahydroisoidol.

0.015 mol of 2-phenyl-4,5,6,7-tetrahydroisonndol in 50 ml of dimethylformamide is cooled for 30 minutes with a mixture of ice and salt, then iricaped with stirring 0.015 mol freshly dried1 | phosphorus oxychloride, maintaining the reaction temperature not higher than - 10 ° C. Then, with eiertic stirring, the temperature of the mixture is brought to room temperature and boiled for 3 hours, then the mixture is cooled to 0 ° C, treated with 30 g of crushed ice and neutralized with hydrochloric acid after decomposition of hydrochloric phosphorus oxide saturated bicarbonate solution

sodium, ensure that the temperature of the mixture does not exceed 2 ° C. When standing and cold, an oil is precipitated, which is extracted with ether. The ethereal extract is washed with water and cyinaT with prokalepny magnesium eulphate. After removing the solvent, yellow needles are obtained. Output 75%, so pl. 75-76 ° C (from n-heptane). The ether solution has a pink-green fluorescence.

Found,%: C 80.23, 79, 88; H 6.76, 6.90; N 6.46, 6.35.

CisHtsNO.

Calculated,%: C 79.97; H 6.71; N 6.22.

Semikarbazoi, so pl. 172-174 ° C.

Subject invention

Claims (2)

1. A method for preparing 2-aryl-4,7-dihydro (or 4,5,6,7-tetrahydro) isoindole form derivatives, characterized in that 2-aryl-4,7 dihydro (or 4,5,6,7-tetrahydro ) -isoindole is subjected to interaction with phosphorus oxychloride in dimethylformamide under cooling, followed by separation of the target product in a known manner. 2. A method according to claim 1, characterized in that the process is carried out at (+5) - (-10) ° C.