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Chemical Structure| 1193-62-0 Chemical Structure| 1193-62-0
Chemical Structure| 1193-62-0

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Product Details of Methyl 1H-pyrrole-2-carboxylate

CAS No. :1193-62-0
Formula : C6H7NO2
M.W : 125.13
SMILES Code : O=C(C1=CC=CN1)OC
MDL No. :MFCD00817048
InChI Key :VONGYFFEWFJHNP-UHFFFAOYSA-N
Pubchem ID :136930

Safety of Methyl 1H-pyrrole-2-carboxylate

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

Application In Synthesis of Methyl 1H-pyrrole-2-carboxylate

* 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.

  • Downstream synthetic route of [ 1193-62-0 ]

[ 1193-62-0 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 1193-62-0 ]
  • [ 1189-71-5 ]
  • [ 937-18-8 ]
  • [ 937-19-9 ]
  • 2
  • [ 1193-62-0 ]
  • [ 26346-85-0 ]
  • methyl 1-[2-(2,4-dimethylphenyl)-2-oxoethyl]pyrrole-2-carboxylate [ No CAS ]
  • 3
  • [ 1193-62-0 ]
  • [ 1189-71-5 ]
  • [ 937-18-8 ]
YieldReaction ConditionsOperation in experiment
45.4% In acetonitrile; at -20 - 25℃; for 20.0833h; 4-Cyano-lH-pyrrole-2-carboxylic acid methyl ester was prepared as described in Can. J. Chem., 59, 2673-76 (1981). lH-Pyrrole-2-carboxylic acid methyl ester (2.00 g, 16.00 mmol) was dissolved in acetonitrile (5 mL) and the solution was cooled to -20 0C. Chlorosulfonylisocyanate (3.40 g, 24.00 mmol) was dissolved in acetonitrile (5 mL) and added dropwise via syringe over a period of 5 min to the above solution. The solution was allowed to warm to 25 0C and was stirred for 20 h. The solution was cooled back to 0 0C, NN-dimethylformamide (2 mL) was added and the solution was heated to 50 0C for 15 min. The reaction mixture was poured into ice and was extracted with chloroform, washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm, 40% ethyl acetate in hexanes) afforded the desired product, 4-cyano-lH-pyrrole-2- carboxylic acid methyl ester (1.09 g, 7.265 mmol, 45.4% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ: 3.91 (3H, s), 7.12 (IH, t, J= 2.0 Hz), 7.40 - 7.41 (IH, m), 9.60 (IH, bs). FT-IR (ATR) vmax (neat): 2228, 1691 cm"1.
  • 4
  • [ 67-56-1 ]
  • [ 1193-62-0 ]
  • [ 59237-53-5 ]
  • [ 1236119-77-9 ]
YieldReaction ConditionsOperation in experiment
92% Methyl 1H-pyrrole-2-carboxylate (5.78 g, 46.2 mmol) was dissolved in DMSO and cooled to 10° C. NaH was added in two portions over 5 min. The reaction mixture was stirred at 10° C. for 10 min and <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (5 g, 23.09 mmol) in DMSO (10 mL) was added slowly over 3 min. The red reaction mixture was allowed to warm to room temperature and stirred overnight. It was cooled to 0° C. and quenched with water (12 mL) and diluted with brine (50 mL). The mixture was washed with EtOAc (2.x.25 mL) and the aqueous layer was acidified to pH=2 with 4.5 N HCl. It was extracted with EtOAc (1.x.100 mL) and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo to afford a yellow solid, which was dissolved in MeOH (100 mL) and cooled to 0° C. Thionyl chloride (45 mL, 617 mmol) was added slowly over 5 min. The reaction mixture was stirred at 0° C. for 1 h and then at room temperature overnight. It was concentrated in vacuo and the resulting solid was triturated with ethyl acetate (300 mL). The solid was filtered off and the filtrate was concentrated in vacuo. then washed with ethyl ether to afford methyl 6-(2-(methoxycarbonyl)-1H-pyrrol-1-yl)-5-nitronicotinate (5.04 g, 16.51 mmol, 92percent yield) as a yellow solid, [M+H] calc'd for C13H11N3O6, 306; found, 306.
  • 5
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  • [ 1189-71-5 ]
  • [ 937-19-9 ]
  • 6
  • [ 1193-62-0 ]
  • [ 230299-21-5 ]
  • [ 1451144-92-5 ]
  • 7
  • [ 1193-62-0 ]
  • [ 399-25-7 ]
  • C14H12ClFN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With aluminum (III) chloride; In dichloromethane; at 0 - 20℃; for 12h; Anhydrous AlCl3 (2.35g, 18mmol) was suspended in anhydrous CH2Cl2 (30mL),Cool to 0C, add 2-fluoronitrostyrene (6mmol), 2a (6mmol), r.t for 12h,The organic phase was washed with a saturated NaCl aqueous solution, dried, and the solvent was distilled off to obtain 3c, which was directly used in the next reaction.NiCl2·6H2O (6 mmol) was added to methanol (25 mL) in which compound 3c was dissolved, and stirred under ice bath conditions for 5 min, NaBH4 (24 mmol) was added, and the ice bath was reacted for 1 h.At the end of the reaction, add saturated NH4Cl solution (25mL), filter, evaporate the solvent, add HCl (1M) solution to adjust the pH to 4-5, add CH2Cl2 solution to extract twice, retain the aqueous phase, add NaOH (1M) solution to adjust the pH to Alkaline, the organic phase was extracted twice with CH2Cl2, the organic phase was retained, dried over anhydrous Na2SO4 overnight, and the solvent was evaporated to obtain the product, with a total yield of 77% in two steps.
 

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