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Chemical Structure| 658695-84-2 Chemical Structure| 658695-84-2

Structure of 658695-84-2

Chemical Structure| 658695-84-2

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Product Details of [ 658695-84-2 ]

CAS No. :658695-84-2
Formula : C13H11ClN2O3
M.W : 278.69
SMILES Code : O=C(C1=CNC(C(C2=C(Cl)N=CC=C2)=O)=C1)OCC
English Name :Ethyl 5-(2-chloronicotinoyl)-1H-pyrrole-3-carboxylate

Safety of [ 658695-84-2 ]

Application In Synthesis of [ 658695-84-2 ]

* 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 [ 658695-84-2 ]

[ 658695-84-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 37964-17-3 ]
  • [ 49609-84-9 ]
  • [ 658695-84-2 ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: pyrrole-3-carboxylic acid ethyl ester; 2-Chloronicotinoyl chloride With tin(IV) chloride In benzene at 20℃; Stage #2: With hydrogenchloride In water; benzene 11 Ethanol (3.2 mL, 54 mmol) and 4-dimethylamino pyridine (DMAP) (54 mg, 0.45 mmol) were added to a mixture of pyrrole-3-carboxylic acid (500 mg, 4.5 mmol) and dicyclohexylcarbodiimide (1.11 g, [5.] 4 mmol) (Aldrich, Milwaukee, WI) in tetrahydrofuran (THF) (15 mL). After heating at 60 [°C] for 10 hours, the reaction was cooled. The precipitate was filtered off, washed with ethyl acetate, the combined filtrate was concentrated and purified on a silica gel column to give 500 mg (81%) of [LH-PYRROLE-3-CARBOXYLIC] acid ethyl ester as a colorless oil. ['HNMR] (400 MHz, DMSO-d6) 8 [11.] 40 (br s, [1H,] NH), 7.37 (s, 1H), 6.78 (s, [1H),] 6. [38] (s, [1H),] 4.13 (q, J = 7 Hz, 2H), 1.22 (t, [J=] 7 Hz, 3H). Ms m/z 138 [M-1]. A solution of 2-chloronicotinoyl chloride (493 mg, 2.8 mmol) in benzene (1 mL) was added to a mixture of [LH-PYRROLE-3-CARBOXYLIC] acid ethyl ester (390 mg, 2. [8] mmol) in benzene (3 mL), followed by a dropwise addition of tin (IV) chloride (0.5 [ML).] The mixture was stirred at room temperature under nitrogen for overnight. The reaction was treated with 2N HCl and extracted with ethyl acetate. The combined ethyl acetate was washed, dried and concentrated to give 390 mg (50%) [OF 5-(2-CHLORO-PYRIDíNE-3-CARBONYL)-LH-PYRROLE-3-] carboxylic acid ethyl ester as a white solid. 'HNMR (400 MHz, DMSO-d6) 8 12.92 (br s, 1H, NH), 8.57 (s, 1H), 8.05 (d, 1H), 7.80 (s, 1H), 7.57 (m, 1H), 6.78 (s, 1H), 4.16 (q, J= 7 Hz, 2H), 1.21 (t, J= 7 Hz, 3H). MS [M/Z] 279 [[M++IL.] A mixture of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-carboxylic acid ethyl ester (1.2 g, 4.32 mmol) and hydrazine hydrate (6.27 mL) in ethanol (50 mL) was heated at 80 °C for 24 hours. The reaction was concentrated and the residue was neutralized to pH 7 with 1N [HC1,] extracted with ethyl acetate. The combined ethyl acetate was dried, concentrated and purified on a silica gel column to give the titled compound as a white solid. [IHNMR] (400 MHz, DMSO-d6) 8 13.70 (s, 1H, NH), 12.16 (br s, [1H,] [NH),] 8.52 (m, 2H), 7.46 (s, [1H),] 7.21 (m, [1H),] 7.04 (s, 1H), 4.2 (q, 2H), 1. [28] (t, 3H). MS [M/Z] 257 [[M++1].]
 

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