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[ CAS No. 63475-29-6 ] {[proInfo.proName]}

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Chemical Structure| 63475-29-6
Chemical Structure| 63475-29-6
Structure of 63475-29-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 63475-29-6 ]

CAS No. :63475-29-6 MDL No. :MFCD05258142
Formula : C13H14N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 246.26 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 63475-29-6 ]

* 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 [ 63475-29-6 ]

[ 63475-29-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 63475-29-6 ]
  • [ 79878-27-6 ]
YieldReaction ConditionsOperation in experiment
85% With hydrazine hydrate; In tetrahydrofuran; for 3h;Reflux; The methyl nalidixate (2 g, 8.17 mmol) was dissolved in tetrahydrofuran (10 mL) and hydrazine hydrate (0.5 mL, 12.25 mmol) was added to it. The contents were refluxed for 3 h. To the resultant reaction mixture, cold water (50 mL) was added and stirred for 10 min. A solid separated out which was filtered at pump and dried to give nalidixic acid hydrazide (1.7g, 85%).
85% With hydrazine hydrate; In tetrahydrofuran; at 80 - 90℃; The above synthesized ester (2 g) dissolved in tetrahydrofuran(10 mL) and to this hydrazine hydrate (0.5 mL) wasadded. The contents were refluxed for 3 h. To the mixture,cold water (50 mL) was added and stirred for 10 mins. A solidseparated out which was filtered at pump and dried to givenalidixic acid hydrazide (85 %).
With hydrazine hydrate; In tetrahydrofuran; for 3h;Reflux; The above synthesized ester (2 g) was dissolved in tetrahydrofuran (70 ml)in a 250 ml round bottom flask and NH2NH2.H2O (0.8 ml)was added. The contents were refluxed for 3 h. To the resultant reaction mixture, cold water (100 ml) was added and stirred for 30 min. A solid separated out was filtered at pump and dried.
1.6 g With hydrazine hydrate; In tetrahydrofuran;Reflux; To a solution of methyl nalidixate (1) (2 g, 8.17 mmol) in tetrahydrofuran (10 mL), hydrazine monohydrate (0.5 mL,12.25 mmol) was added and the contents were heated under reflux for 3-4 h. After completion of the reaction, cold water(50 mL) was added to the mixture with stirring. A solid mass deposited was filtered, washed with water, dried and recrystallized in ethanol to furnish the desired compound 2 (1.60 g)as cream colored crystals. IR (cm-1, numax, KBr): 2925, 2977(C-H of aliphatic), 1675 (C=O of CONH), 1615 (C=O of aromatic ring) 1603, 3308 (NH of CONH), 3325 (free NH2),1472 (N-N of NHNH2). 1H NMR (300 MHz, DMSO-d6,TMS): delta1.06 (t, 3H, N1 CH2CH3), 2.46 (s, 3H,C7 CH3), 4.73(q, 2H, N1 CH2CH3), 6.94 & 7.48 (d, J=9.2 Hz, 2H, Ar), 8.45(s, 1H, Ar), 9.18 (s, IH, CONH). 13C NMR (75 MHz,DMSO-d6):delta 15.35 (N-CH2CH3), 27.01 (CH3), 46.20 (NCH2CH3),122.54, 123.12, 125.09, 126.17, 164.25 (C=O),180.40 (C=O).
With hydrazine hydrate; In ethanol; for 5h;Reflux; A mixture of 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid (1) [1.0 g;4.305 mmoles], dimethylsulphate [0.81 mL, 6.46 mmol],potassium carbonate [2.98 g; 21.5-mmol] and tetrahydrofuran(25 mL) was refluxed for five hours. Contents were cooled to25C and the ester formed was extracted with chloroform,dried over sodium sulphate and was precipitated out. Methyl1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate thusobtained (2) [1.0 g; 4.08 mmoles] and hydrazine hydrate [70%;0.48 g; 6.12 mmol] was refluxed in ethanol [50 mL] for fivehours till completion of the reaction.26) Contents were cooled,neutralized with dilute hydrochloric acid and concentrated byevaporation of ethanol till the settling of precipitates. Precipitateswere washed with water and crystallized from ethanol.mp 185-187C; Lit. mp 186-188C.27) Yield 78%.

  • 2
  • [ 77-78-1 ]
  • [ 389-08-2 ]
  • [ 63475-29-6 ]
YieldReaction ConditionsOperation in experiment
95% To the solution of nalidixic acid (2 g, 8.611 mmol) in tetrahydrofuran (50 mL) anhydrous potassium carbonate (5.96 g, 43.05 mmol) was added and stirred for 1 h. After 1 h dimethyl sulphate (1.63 mL, 12.92 mmol) was added to it and refluxed at 70 C. After refluxing, the solvent was removed under reduced pressure on a rotary evaporator and the product was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to give methyl nalidixate (1.95 g, 95%).
The 1-ethyl-7-methyl-4-oxo-1, 8 naphthyridine-3-carboxylic acid 2 g was dissolved in tetra hydro furan and then5.96 g of anhydrous potassium carbonate was added and stirred for an hour. Subsequently after the addition of1.63 mL dimethyl sulphate the contents were refluxed at80 C for 4 h and the reaction was monitored byTLC. As the reaction progressed, the new spot is observedat lower RF value. The solvent was removedwith the help of rotary evaporator, the product was extractedwith 70 % ethyl acetate and it was filtered undervacuum pump and dried.
Nalidixic acid (3 g) and tetrahydrofuran (100 ml) were placed ina 250 ml round bottom flask and mounted over a magnetic stirrer. Anhydrous potassium carbonate (8.96 g) was added and the contents were stirred for one hour. Dimethylsulfate (2.475 ml) was added to this stirred solution andthe mixture was refluxed at 70-80 C. The progress ofthe reaction was monitored by TLC using hexane/ethylacetate (80:20) as the eluent. After 6 h the new spot isobserved on TLC plate. After the completion of reactionthe solvent was removed under reduced pressure on arotary evaporator and the product was extracted with ethylacetate. The ethyl acetate layer was dried over anhydroussodium sulfate and concentrated under reduced pressureto give the desired ester.
1.9 g A mixture of nalidixic acid (2 g, 8.61 mmol), anhydrous potassium carbonate (5.96 g, 43.05 mmol) and tetrahydrofuran (50 mL) was stirred for 1h. Then, dimethyl sulphate (1.63 mL, 12.92 mmol) was added to it and the reaction mixture was refluxed for 2h. After refluxing, the solvent was removed under reduced pressure and the product was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to furnish nalidixic acid methyl ester 1(1.90 g) [17]. The spectral and physical data of 1 was found to be in agreement with the reported values [18].
With potassium carbonate; In tetrahydrofuran; for 5h;Reflux; A mixture of 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid (1) [1.0 g;4.305 mmoles], dimethylsulphate [0.81 mL, 6.46 mmol],potassium carbonate [2.98 g; 21.5-mmol] and tetrahydrofuran(25 mL) was refluxed for five hours. Contents were cooled to25C and the ester formed was extracted with chloroform,dried over sodium sulphate and was precipitated out. Methyl1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate thusobtained (2) [1.0 g; 4.08 mmoles] and hydrazine hydrate [70%;0.48 g; 6.12 mmol] was refluxed in ethanol [50 mL] for fivehours till completion of the reaction.26) Contents were cooled,neutralized with dilute hydrochloric acid and concentrated byevaporation of ethanol till the settling of precipitates. Precipitateswere washed with water and crystallized from ethanol.mp 185-187C; Lit. mp 186-188C.27) Yield 78%.

  • 3
  • [ 2582-30-1 ]
  • [ 63475-29-6 ]
  • 3-(5-amino-2H-1,2,4-triazol-3-yl)-1-ethyl-7-methyl-1,8-naphthyridin-4(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sodium methylate; In methanol; for 25h;Reflux; General procedure: Aminoguanidine bicarbonate (5.04 g, 0.04 mol) was added portionwiseto a stirred ice cooled methanolic solution (30 ml) of freshly preparedsodium methoxide (0.84 g, 0.04 mol). A solution of the respectivenalidixic acid methyl ester (2) or 6-bromo-nalidixic acid methyl ester(3) (0.01 mol) in methanol (10 ml) was then added dropwise. The icebath was removed and the mixture was refluxed for 25 h, poured intocooled water and neutralized (pH?7) with 3 N HCl. The precipitatedproduct was filtered, washed with water, dried and crystallized frommethanol.
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