SU1382835A1 - 3-methylpyrimido /1,2-a/indol-2-ons as intermediate products in synthesis of 3-methyl-10-a-styrilpyrimido-/1,2-a/indol-2-ons - Google Patents

Abstract

The invention relates to heterocyclic substances, in particular 3.8, 10, 10, 10a-pentamethyl- or 3, JO, 0, 10-a-tetramethyl-, 2, 3, 4, 10, JO-a-hexahydropyrimido 1,2 -and indol-2-dreams, for the synthesis of 3-methyl-10-a-styrylpyrimido 1,2-a indol-2-ones - the color-forming components of information recording systems and dyes for synthetic fibers. The goal is to create new intermediate substances that provide the best yield of the target products and reduce the consumption of methacrylamide. Synthesis is carried out from hydrochloride 2 (3) 3,3-tri (tetra) methyl-3H-indol and methacrylamide in medium at 100 ° C, followed by treatment with KOH and extraction with ether. Yield,%: mp. &Amp; gross-la: a) 30; 114-115; C ,, 0, b) 27; 157-158; CjjH jNjjO. Synthesis of color-forming components from these substances ensures their high yield (83 and 85%), i.e. 2-3 times higher than the known, and reduces 4-5 times the consumption of methacrylamide. with (L

Description

with

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Yu

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with

SP

113828

The invention relates to new compounds of 3-methylpyrimne to 1, 2-a t-indol-2 one of the general formula

where R is hydrogen or methyl, which can be used to synthesize 3-methyl-III-a-styrylpyrimi- to 1, 2 - aTindol-2 ones, the color-forming component of information recording systems and dyes for synthetic fibers.

The purpose of the invention is the creation of new starting materials for the synthesis of 3-methyl-10-a-c tyrylpyrimido, 2-a-indol-2-ones, providing a higher yield of the target products and reducing the consumption of methacrylamide.

Example 1. 3, J05, JO, ramethyl-, 2,3,4,10, J 0-a-hexahydropyrimido G1,2-a indol-2-one.

A mixture of 5.87 g (0.03 mol) of 2,3,3 trimethyl-ZN-indole hydrochloride and 3.87 g (0.045 mol) of methacrylamide is heated in 12 ml of acetic acid for 8 hours at. The mixture is boiled in water, 5% potassium hydroxide solution is added to alkaline reaction and extracted with ether (2x25 m. The extract is washed with water (2x20 ml) and dried with calcium chloride. The solvent is distilled off and the residue is crystallized from 3-5 ml of ether at (10) - (5) ° C. Obtain 2.20 g (30.0%) of 3-methylpyrimido tl, 2-a 1 indol-2-one, mp 114-115 C (from acetone), Found,%: C, 73.96; n, 8.33; K, 11.67. Particular. Calculated,%: C, 73.74; H, 3.25;

And L, D6.

PMR spectrum (CDCl, cf) ppm: 1.13 s. (3N, 10-CH,); 1.2 d. (3N, 3-SP); 1.36 s, (3N, 10-CH); 1.53 seconds (ZN, 10a-CH) j 2.35-3.95 (ZN, CH, - CH) | 6.70 broad s (W, NH) 6.57-7.31 m (4H-CH pro,).

IR spectrum (KBG), 1660 (), 3190 (S). P r and me 2. R 2.8,10,10,10-a-Pentamethyl-1, 2,3,4,10,10 a-hexa-hydropyrimido 1, 2-a indol 2-one.

c 5

ZO. .,.

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The reactions of 6.29 g of 10.03 mol) hydroxy / jurida 2 5 3 зЗ} 5-tetramethyl-3N-nidol with 3s87 (0.045 mol) of methacrylamide in 12 ml of acetic acid are carried out as described in Example J, except that the reaction;) the mixture is treated with a solution of sodium hydroxide. 2.10 i- (27.0%) 3 methylpy are obtained; rimido 1, 2-a indole 2-one, tlsh. 57 J58 C (from acetone). Found u,%: K 11.0.

c ,, n ,, o ,,

Calculated,%: N 10,84. Spectrum PIR (SVS1z, cf), ppm: 1.09 s. (ZN, lO-CttJ; 1.15 d. (ZN, 3-CH,); 1.34 s. (ZN, 0-CH); i, 50 s (ZN, Yua-CH,); 2.29 с, (ЗН, 2.33-4.00 m (ЗН, СН5СН); 5.90 br. s, (1Н, КN); 6.50-7.05 m. (ЗН, СН "p" „) .

PRI me R 3. 1O- (p-Dimethyl-aminosityl) -3.0-10-a-trimethyl-1,2, 3,4,10,10a-hexahydropyrimido D, 2-aj INDOL-2- CH.

A solution of 2.44 g (0.01 mol) of 3-methyl pyrimido, 2 a indol-2-one and 1.49 g (C, 01 mol) of p-dimethylaminobenzalde. In a mixture of 1 2 ml of acetic acid Y : 0.3 ml of acetic anhydride is heated for 1 hour at 95-100 ° C. The mixture is poured over 8 water and treated with a 5% potassium hydroxide solution until alkaline, the vat is filtered, dried and crystallized from acetone. Compound yield 3.10 g (83%), mp. 208-.

Found,%: N 1 1, 24.

With „Н5,1ЬО

Calculated,%: N 11,19.

PMR spectrum (CDCl, t), ppm: 1.13 d. (3N, 3-CH,); 1.19 s. (ZN, 10-CHj: 35 s. (ZN, 10-CH.); 2.43- 3.88 m. (ZN, CHCHj; 3.00 s. (6H, CH-jNCH): 6, 10 -7, 43 m (un,

 and p about. l, 8 and

II p c: Mp 4, IQ-a (p-Dimethyl-aminostyryl) ™ 3.8, JO, 10-a tetramethyl I 5 2,3,4 51 O, 10-a-hexahydropy-, 2 And indole-2-he.

The reaction of 2.58 g (0.01 mol) of tilpyrimido Icdol-2-one with 1.49 g (OjOi mol) of p-dimethylaminobenzyshdehyde is carried out as in Example 3. The yield of the compound is 3.30 g (85%), mp. . 216 217 C.

Found,%; N 10.50.

Cjj

Calculated J%; N 1 Oh, 78,

PMR spectrum (CDCl ,, with /), ppm : J, 10 d. (ZN, Z-CH,); 1.15 s. (MN, lO-CH,); J, 30 s. (3N, 10-CH3); 2.30 s. (3N, 8-СНз); 2.43-3.88 m. (3N, CHCH2); 3.00 s. (6H, CHjNCHj); 6.08-7.43 mL9N, CH „ro“, bmnil. ).

The use of the described compounds makes it possible to increase the yield of 3-methyl-10-a-styryl pyrimido C1,2-aJ indol--2-one by 2-3 times (by 2,3,3-trimethyl - 3N - indole) and reduce - consumption of methacrylamide in 4 - 5 times.

Claims (1)

The invention claims 3-Methylpirkmido G, 2-a indol-2-ones of the general formula SNS NH 0 CH3 where R is hydrogen or methyl, as intermediates in the synthesis of 3-methyl-10-a-styrylpyrimi- to 1, 2-a indol-2-ones,