Structure of 1072-87-3
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CAS No. : | 1072-87-3 |
Formula : | C5H5NO2 |
M.W : | 111.10 |
SMILES Code : | O=C(C(C)=C1)NC1=O |
MDL No. : | MFCD10699598 |
InChI Key : | ZLPORNPZJNRGCO-UHFFFAOYSA-N |
Pubchem ID : | 95941 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With sodium hypochlorite; sodium hydroxide; In water; at 0℃; for 4h;Inert atmosphere; | To a mixture of NaOCl solution (4.99%, 10 mL) and NaOH (1.6 g, 40mmol) cooled at 0 C was added dropwise a precooled (0 C) solution of <strong>[1072-87-3]3-methylpyrrole-2,5-dione</strong> (3.55 g, 32 mmol) in H2O (14 mL). The reaction mixture was then stirred at the same temperature for 4 h to obtain a clear solution. After completion of reaction (monitored by TLC), dilute H2SO4 was added until pH 3 to form a white precipitate, which was filtered and dried to obtain the desired product as a white solid; yield: 1.8 g (44%); mp 115-117 C.IR (KBr): 2970, 2910, 2162, 1753, 1172, 813, 549 cm-1.1H NMR (400 MHz, DMSO-d6): δ = 1.67-1.87 (m, 3 H), 7.38-7.55 (m, 1H), 11.16-11.47 (m, 1 H).13C NMR (100 MHz, CDCl3): δ = 161.2, 148.9, 141.6, 103.1, 11.9.MS (ESI): m/z = 125.8 (M - H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; for 4h; | To a solution of <strong>[1072-87-3]citraconimide</strong> (26) (4.50 g, 40.5 mmol) in ethanol (50 mL) 10% palladised charcoal (2.00 g) was added. The suspension was hydrogenated under atmospheric pressure for 4 h. After completion of the reaction (confirmed with TLC) the mixture was filtered through a pad of Celite, the Celite layer was washed with ethanol (2 _ 20 mL), and the filtrate was evaporated under reduced pressure, giving the title compound 27 as a white crystalline solid (4.55 g, 99%), mp 57-59 C (lit.: 65 C) [42]; Rf (DCM:MeOH 10:1) 0.52; nmax (KBr) 3201, 3071, 2766, 1763, 1707, 1352, 1206, 1176, 1037 cm_1; 1H NMR (400 MHz; DMSO-d6) d (ppm) 1.16 (3H; d; J 7.2 Hz; C(3)-CH3); 2.26 (1H; m; 2J_17.7 Hz (Ha-4), 3J 5.1Hz (H-3); Hb-4); 2.78 (1H; m; 3J 9.2 Hz (H-3); Ha-4); 2.81 (1H; m; 3J 7.3 Hz (C(3)-CH3); Ha-4); 10.94-11.10 (1H; br; NH-1); 13C NMR (101 MHz; DMSO-d6) d (ppm) 15.7 (C(3)-CH3); 35.4 (C-3); 37.1 (C-4); 178.0 (C-5); 182.2 (C-2); HRMS: M 113.0461 (delta _14.2 ppm; C5H7NO2); HR-EI-MS (rel. int. %): 113(100); 70(77). |
With palladium on activated charcoal; hydrogen; | All of the chemicals were commercially available, exceptfor racemic (5S)-2-methyl-5-(prop-1-en-2-yl) cyclohex-anone (P3), dimethyl 2-methylsuccinate (P15), methyl2-acetamidopropanoate (P16) and 3-methyl-2,5-Pyrrolidinedione(P30), which were obtained by Pd/C-catalyzed hydrogenation of (S)-carvone (S3), dimethyl itaconate (S15), methyl2-acetamidoacrylate (S16) and 3-methyl maleimide (S30),respectively [23]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 1,1,1,3,3,3-hexamethyl-disilazane; In N,N-dimethyl-formamide; at 100℃; for 1h; | To a solution of citraconic anhydride (25) (12.0 g, 107 mmol) in DMF (100 mL) at 100 C hexamethyldisilazane (34.2 mL, 160 mmol) was added. The mixture was stirred at 100 C for 1 h, then it was cooled to room temperature. The solvent was evaporated under reduced pressure. The crude product was recrystallized from a mixture of hexane and ethyl acetate to give the title compound 26 as a white crystalline solid (8.33 g, 70%), mp 104-105 C (lit.: 104-105 C) [3]; Rf (DCM:MeOH 10:1) 0.71; nmax (KBr) 3271, 3098, 2674, 1844, 1778, 1764, 1712, 1634, 1342, 1284, 1175, 1090 cm_1; 1H NMR (500 MHz; DMSO-d6) d (ppm) 1.94 (3H; d; J 1.8 Hz; C(3)-CH3); 6.50 (1H; q; J 1.8 Hz; H-4); 10.72 (1H; br s; NH-1); 13C NMR (126 MHz; DMSO-d6) d (ppm) 10.2 (C(3)-CH3); 128.0 (C-4); 145.9 (C-3); 172.2 (C-5); 173.1 (C-2); HRMS: M 111.0311 (C5H5O2N; delta _8.1 ppm); HR-EI-MS (rel. int. %): 111(100); 83(8); 68(39). |
40% | With 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; N,N-dimethyl-formamide; at 0 - 20℃; for 20.3333h; | Stage 1: 3-methylpyrrole-2,5-dione A solution of hexamethyldisilazane (80.7 g, 104.8 ml, 500 mmol) in methanol was added dropwise to a solution of citraconic anhydride (5.60 g, 4.49 ml, 50 mmol) in N,N-dimethylformamide (170 ml) at 0 C. The reaction solution was stirred at room temperature for 20 h, thereafter methanol (100 ml) was added and the mixture was stirred for a further 20 min. The solvent was concentrated in vacuo and the residue was taken up in a mixture of ethyl acetate/water (150 ml:50 ml). The organic phase was separated off, washed with water (2*50 ml), sodium bicarbonate solution (50 ml) and with water again (50 ml) and then dried with sodium sulfate. The solvent was concentrated and the residue was dried in vacuo. Yield: 2.30 g (40%), white solid Melting point: 100-102 C. [lit. 101-104 C. (K. R. Shah, C. DeWitt Blanton, J. Org. Chem. 1982, 47, 502)]. |
32% | With urea; In sulfolane; at 180℃; for 1h;Product distribution / selectivity; | 25 g (0.219 mol) of 2-methyl succinic anhydride were heated in 37.5 g of sulfolane to a reaction temperature of 180 C. After the reaction temperature was achieved 18.95 g (0.32 mol) of urea were spread in and stirring was continued for 1 h at the reaction temperature under flushing with N2. Following cooling, the reaction mixture was first added with 2-propanol and then with MTBE. 6.5 g of 2-methyl succinic imide (32% of the theoretical yield) were obtained |
20% | With urea; In diethyleneglycol diethylether; at 180℃;Product distribution / selectivity; | EXAMPLE 25 In a manner analogous to that of Example 24, diethyleneglycol diethylether was used as the solvent at 180 C. After cooling, first MTBE was added. From the resulting oil 2-methyl succinic imide was obtained in a yield of 20% by recrystallization from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 - 0℃; for 1.5h;Inert atmosphere; | To a solution of <strong>[1072-87-3]citraconimide</strong> (26) (1.00 g, 9.00 mmol) in THF (50 mL) under nitrogen at _78 C diisobutyl aluminium hydride solution (10.7 mL, 16.0 mmol, 25 wt % in toluene) was added via a syringe. The mixturewas let towarm up to 0 C and it was stirred at this temperature for a further 90 min, then it was quenched with a mixture of methanol (25 mL) and water (25 mL). The solvents were evaporated under reduced pressure, then the crude product was triturated in ethyl acetate. The suspension was filtered, the filtrate was dried (Na2SO4) and evaporated under reduced pressure to give the title compound 1 as a white crystalline solid (930 mg, 91%), mp 115-117 C (lit.: 115-118 C) [5]; Rf (DCM:MeOH 10:1) 0.42; nmax (KBr) 3244, 2985, 2931, 1688, 1650, 1409, 1306, 1281, 1216, 1058 cm_1; 1H NMR (500 MHz; CD3OD) d (ppm) 1.83 (3H; dd; J 1.7; 1.4 Hz; C(3)-CH3); 5.44 (1H; dq; 1.7; 1.4 Hz; H-5); 6.63 (1H; ~qui; J 1.7 Hz; H-4); 13C NMR (126 MHz; CD3OD) d (ppm) 10.6 (C(3)-CH3); 80.0 (C-5); 136.9 (C-3); 143.1 (C-4); 175.5 (C-2); HRMS: M+H 114.05495 (delta _0.04 ppm; C5H8O2N); HR-ESI-MS-MS (CID 55%, rel. int. %): 97(100). |
A390889 [1823773-11-0]
3,3'-(Ethane-1,2-diyl)bis(1H-pyrrole-2,5-dione)
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