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Chemical Structure| 872714-50-6 Chemical Structure| 872714-50-6

Structure of 872714-50-6

Chemical Structure| 872714-50-6

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Product Details of [ 872714-50-6 ]

CAS No. :872714-50-6
Formula : C13H12BrNO3
M.W : 310.14
SMILES Code : CCOC(=O)C1=C(Br)C2=C(C=CC(OC)=C2)N=C1
MDL No. :MFCD16987484

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Application In Synthesis of [ 872714-50-6 ]

* 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 [ 872714-50-6 ]

[ 872714-50-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 77156-78-6 ]
  • [ 872714-50-6 ]
YieldReaction ConditionsOperation in experiment
95% c) Ethyl 4-bromo-6-(methyloxy)-3-quinolinecarboxylate; To a vigorously stirred solution of ethyl 4-bromo-6-(methyloxy)-3- quinolinecarboxylate (10 g, 40.5 mmol) in DMF (40 mL) was added PBr3 (4.4 ml_, 42.5 mmol) via dropwise addition over 15 min at rt. The reaction was allowed to stir at ambient temperature for 45 min after which was added water (150 mL). The reaction was neutralized with aq. NaHCC>3. The solid was collected by filtration and washed with water and dried under vacuum to give the desired product (12 g, 95%).
78% With phosphorus tribromide; In N,N-dimethyl-formamide; at 0 - 20℃; for 3.5h; PBr3 (64.5 g, 22.5 mL, 0.239 mole) was added dropwise to a stirred, ice cold suspension of <strong>[77156-78-6]4-hydroxy-6-methoxy-quinoline-3-carboxylic acid ethyl ester</strong> (59 g, 0.239 mole) in DMF (750 mL); the temperature rose to 15-20 0C for 30 min and then dropped to ca. 5 0C (the starting material dissolved fairly quickly and a new solid precipitated out). EPO <DP n="21"/>After 3 hr the solid was collected, washed sequentially with cold DMF, hexane, and water, then was dried at 40 0C in vacuo overnight to give the title compound (41 g, 78%): LC/MS (ES) /77/e 310/312 (M + H)+.
78% With phosphorus tribromide; In N,N-dimethyl-formamide; at 0 - 20℃; for 3h;Product distribution / selectivity; b) 4-Bromo-6-methoxy-quinoline-3-carboxylic acid ethyl ester; PBr3 (64.5 g, 22.5 mL, 0.239 mole) was added dropwise to a stirred, ice cold suspension of <strong>[77156-78-6]4-hydroxy-6-methoxy-quinoline-3-carboxylic acid ethyl ester</strong> (59 g, 0.239 mole) in DMF (750 mL); the temperature rose to 15-20 0C for 30 min and then dropped to ca. 5 C (the starting material dissolved fairly quickly and a new solid precipitated out). After 3 hr the solid was collected, washed sequentially with cold DMF, hexane, and water, then was dried at 40 0C in vacuo overnight to give the title compound (41 g, 78%): LC/MS (ES) m/e 310/312 (M + H)+.
78% With phosphorus tribromide; In N,N-dimethyl-formamide; at 0 - 20℃; for 3.5h; b) 4-Bromo-6-methoxy-quinoline-3-carboxylic acid ethyl ester; PBrs (64.5 g, 22.5 ml_, 0.239 mole) was added dropwise to a stirred, ice coldsuspension of <strong>[77156-78-6]4-hydroxy-6-methoxy-quinoline-3-carboxylic acid ethyl ester</strong> (59 g, 0.239mole) in DMF (750 ml); the temperature rose to 15-20 C for 30 min and then dropped toca. 5 C (the starting material dissolved fairly quickly and a new solid precipitated out).After 3 hr the solid was collected, washed sequentially with cold DMF, hexane, and water,then was dried at 40 C in vacuo overnight to give the title compound (41 g, 78%): LC/MS(ES)m/e310/312(M + H)+.
78% With phosphorus tribromide; In N,N-dimethyl-formamide; at 0 - 20℃; for 3.5h; PBr3 (64.5 g, 22.5 mL, 0.239 mole) was added dropwise to a stirred, ice cold suspension of <strong>[77156-78-6]4-hydroxy-6-methoxy-quinoline-3-carboxylic acid ethyl ester</strong> (59 g, 0.239 mole) in DMF (750 mL); the temperature rose to 15-20 0C for 30 min and then dropped to ca. 5 0C (the starting material dissolved fairly quickly and a new solid precipitated out). After 3 hr the solid was collected, washed sequentially with cold DMF, hexane, and water, EPO <DP n="30"/>then was dried at 40 0C in vacuo overnight to give the title compound (41 g, 78%): LC/MS (ES) m/e 310/312 (M + H)+
32 g With phosphorus tribromide; In N,N-dimethyl-formamide; at 20℃; for 1h; To a stirred solution of compound 3 (23 g, 93 mmol) in DMF (91 mL) was added PBr3 (8.8mL, 93 mmol) dropwise at RT. The reaction mixture was stirred at ambient temperature for lh after which 200ml ice cold water was added. The reaction was neutralized with aq. NaHC03 solution. The obtained solids were collected by filtration, washed with water and dried under vacuum to give the required product 4 (32 g).

 

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