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Chemical Structure| 19733-96-1 Chemical Structure| 19733-96-1

Structure of 19733-96-1

Chemical Structure| 19733-96-1

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Product Details of [ 19733-96-1 ]

CAS No. :19733-96-1
Formula : C8H9NO2
M.W : 151.16
SMILES Code : O=C(O)CC1=CC=C(C)N=C1
MDL No. :MFCD00190601
InChI Key :DWTRPWLHNATUPX-UHFFFAOYSA-N
Pubchem ID :22507698

Safety of [ 19733-96-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 19733-96-1 ]

* 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.

  • Upstream synthesis route of [ 19733-96-1 ]
  • Downstream synthetic route of [ 19733-96-1 ]

[ 19733-96-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 19733-95-0 ]
  • [ 19733-96-1 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With water; sodium hydroxide In ethanol at 80℃; for 17 h;
Stage #2: With hydrogenchloride In water
Example 3: Preparation of 2-methyl-5-pyridinylacetic acid; 2-(6-methylpyridin-3-yl)morpholinylethylthione 25g was dissolved in 200ml of ethanol, then 60percentNaOH aqueous solution (21gNaOH dissolved in 25ml water) was added, heated to 80°C, refluxed for 17h. The reaction stopped, cooled to room temperature, rotary evaporated out solvent. A small amount of water was added for dissolution, adjusted with concentrated hydrochloric acid to reach a PH of 2, suction filtrated out insoluble substance, the filtrate was extracted with ethyl ether twice, the ethyl ether layers were combined and washed with water once. The water layers were collected for standby use. Rotary evaporated out solvent water, placed in vacuum drying oven and dried for 24h to obtain 2-methylpyridinylacetic acid 11 g, yield was about 70percent. 1H-NMR(400MHz,DMSO-d6) δ 2.43(3H,s,CH3);3.57 (2H,s,CH2); 7.17-7.19(1H,d,ArH); 7.53-7.56(1 H,dd,ArH); 8.30-8.31 (1H,d,ArH); 12.42(1H,s,COOH).
70%
Stage #1: With water; sodium hydroxide In ethanol at 80℃; for 17 h;
Stage #2: With hydrogenchloride In water
Example 3Preparation of 2-methyl-5-pyridinylacetic acid2-(6-methylpyridin-3-yl)morpholinylethylthione; 25 g was dissolved in 200 ml of ethanol, then 60percent NaOH aqueous solution (21 g NaOH dissolved in 25 ml water) was added, heated to 80° C., refluxed for 17 h. The reaction stopped, cooled to room temperature, rotary evaporated out solvent. A small amount of water was added for dissolution, adjusted with concentrated hydrochloric acid to reach a PH of 2, suction filtrated out insoluble substance, the filtrate was extracted with ethyl ether twice, the ethyl ether layers were combined and washed with water once. The water layers were collected for standby use. Rotary evaporated out solvent water, placed in vacuum drying oven and dried for 24 h to obtain 2-methylpyridinylacetic acid 11 g, yield was about 70percent.1H-NMR (400 MHz, DMSO-d6) δ 2.43 (3H, s, CH3); 3.57 (2H, s, CH2); 7.17-7.19 (1H, d, ArH); 7.53-7.56 (1H, dd, ArH); 8.30-8.31 (1H, d, ArH); 12.42 (1H, s, COOH).
46%
Stage #1: With water; sodium hydroxide In ethanol for 16 h; Reflux
Stage #2: With hydrogenchloride In ethanol; water
Crude 2-(6-methyl-pyridin-3-yl)-1-morpholin-4-yl-ethanethione (39.5 mmol, 9.685 g) was suspended in 2: 1 H2O/EtOH (40 ml_). NaOH (3.3 eq., 1 18.5 mmol, 4.8 g) was added and the reaction heated to reflux for 16 hours. The volatiles were then removed from the cooled reaction medium, and the pH adjusted to precisely pH 7.0 with 3.0 M HCI. The solvent was removed and the residue slurried in boiling methanol, filtered whilst hot, and the filtrate evaporated to dryness. This crude product contains residual free morpholine, which was removed by flash column chromatography, eluting with 9:1 EtOAc/MeOH. The fractions were analysed by TLC eluting with 1 :1 EtOAc/MeOH (Rf = 0.209). The product was obtained in 46percent yield.δH (250 MHz, CD3OD) 8.33 (1 H, s, Ar), 7.69 (1 H, d, J 7.9, Ar), 7.28 (1 H, d, J 7.9, Ar), 3.59 (2H, s, CH2), 2.51 (3H1 s, CH3); δc (62.5 MHz, CD3OD) 176.6 (C=O), 157.1 (Ar), 150.0 (Ar), 140.3 (Ar), 131.4 (Ar), 125.0 (Ar), 40.3 (CH2), 23.3 (CH3).
References: [1] Patent: EP2417973, 2012, A1, . Location in patent: Page/Page column 6-8; 16.
[2] Patent: US2012/122914, 2012, A1, . Location in patent: Page/Page column 5.
[3] Patent: WO2010/67085, 2010, A2, . Location in patent: Page/Page column 60-61.
  • 2
  • [ 90610-06-3 ]
  • [ 19733-96-1 ]
References: [1] Patent: WO2010/86403, 2010, A1, . Location in patent: Page/Page column 101-102.
  • 3
  • [ 36357-38-7 ]
  • [ 19733-96-1 ]
References: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 704,707.
[2] Patent: EP2417973, 2012, A1, .
[3] Patent: US2012/122914, 2012, A1, .
  • 4
  • [ 5470-70-2 ]
  • [ 19733-96-1 ]
References: [1] Patent: EP2417973, 2012, A1, .
[2] Patent: US2012/122914, 2012, A1, .
  • 5
  • [ 3430-13-5 ]
  • [ 19733-96-1 ]
References: [1] Patent: WO2014/198808, 2014, A1, .
[2] Patent: EP2813505, 2014, A1, .
 

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