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Chemical Structure| 68707-71-1 Chemical Structure| 68707-71-1

Structure of 68707-71-1

Chemical Structure| 68707-71-1

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Product Details of [ 68707-71-1 ]

CAS No. :68707-71-1
Formula : C7H9NO
M.W : 123.15
SMILES Code : OC1=C(C)C(C)=NC=C1
MDL No. :MFCD18384244
InChI Key :PTURTHBRTGJYRN-UHFFFAOYSA-N
Pubchem ID :21702749

Safety of [ 68707-71-1 ]

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

Application In Synthesis of [ 68707-71-1 ]

* 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.

  • Downstream synthetic route of [ 68707-71-1 ]

[ 68707-71-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 68707-70-0 ]
  • [ 68707-71-1 ]
YieldReaction ConditionsOperation in experiment
With water; at 20℃;Heating / reflux; Anhydrous potassium acetate (49 g, 0.5 mol) was added to a solution of2,3-dimethyl-4-nitropyridine (45.6 g, 0.3 mol) prepared in Step 2 in 300 ml of acetic anhydride and then refluxed under stirring for 16 hours. The reaction mixture was cooled to room temperature and then 400 ml of anhydrous ether was added thereto. The reaction mixture was stirred for 1 hour, filtered with Celite, and then concentrated under reduced pressure to give 4-acetoxy-2,3-dimethylpyridine (45 g, 91%). The resulting residue was added to 250 ml of water, refluxed under stirring for 4 hours, and then left overnight at room temperature. The reaction mixture was concentrated under EPO <DP n="56"/>reduced pressure to give 32.6 g of 2,3-dimethyl-4-hydroxypyridine as a liquid form. The liquid product was dissolved in 120 ml of concentrated sulfuric acid and heated to 600C. A mixture of 90% nitric acid (40 ml) and sulfuric acid (30 ml) was slowly added to the reaction mixture for 45 minutes, while maintaining the temperature at 60-650C. The reaction mixture was heated for 2 hours at 65C and then for 30 minutes at 75C. The reaction mixture was cooled to room temperature and then added to ice water. The resulting solution was brought to pH 5-6 with ammonium hydroxide to give a pale yellow solid. The resulting solid was filtered, washed with cold water, and then dried at 80 ~ 900C to give 34.5 g of the titled compound.[757] * H-NMR (CDCl3) delta 2.54(s, 3H), 2.87(s, 3H), 9.35(s, IH)
  • 2
  • [ 68707-71-1 ]
  • [ 68707-72-2 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid; at 60 - 75℃; for 3.25h; Anhydrous potassium acetate (49 g, 0.5 mol) was added to a solution of2,3-dimethyl-4-nitropyridine (45.6 g, 0.3 mol) prepared in Step 2 in 300 ml of acetic anhydride and then refluxed under stirring for 16 hours. The reaction mixture was cooled to room temperature and then 400 ml of anhydrous ether was added thereto. The reaction mixture was stirred for 1 hour, filtered with Celite, and then concentrated under reduced pressure to give 4-acetoxy-2,3-dimethylpyridine (45 g, 91%). The resulting residue was added to 250 ml of water, refluxed under stirring for 4 hours, and then left overnight at room temperature. The reaction mixture was concentrated under EPO <DP n="56"/>reduced pressure to give 32.6 g of <strong>[68707-71-1]2,3-dimethyl-4-hydroxypyridine</strong> as a liquid form. The liquid product was dissolved in 120 ml of concentrated sulfuric acid and heated to 600C. A mixture of 90% nitric acid (40 ml) and sulfuric acid (30 ml) was slowly added to the reaction mixture for 45 minutes, while maintaining the temperature at 60-650C. The reaction mixture was heated for 2 hours at 65C and then for 30 minutes at 75C. The reaction mixture was cooled to room temperature and then added to ice water. The resulting solution was brought to pH 5-6 with ammonium hydroxide to give a pale yellow solid. The resulting solid was filtered, washed with cold water, and then dried at 80 ~ 900C to give 34.5 g of the titled compound.[757] * H-NMR (CDCl3) delta 2.54(s, 3H), 2.87(s, 3H), 9.35(s, IH)
  • 3
  • [ 68707-71-1 ]
  • [ 259807-91-5 ]
YieldReaction ConditionsOperation in experiment
60% <strong>[68707-71-1]2,3-dimethylpyridin-4-ol</strong>, ( 2.0 g, 20 mmol) and phosphorus tribromide oxide (14.0 g, 49 mmol) were left stirring at 1300C for 4 hours under nitrogen. The reaction mixture was poured onto ice and made basic by adding aqueous NaOH. The mixture was then extracted with diethyl ether and water.The brown needle solid was obtained after ether was gently removed (2.03g, purity 90%, yield 60%). 1HNMR (CDCI3): delta ppm 8.10 (d, 1 H), 7.34 (d, 1 H), 2.58 (s, 3H), 2.39 (s, 3H). LC/MS: rt (5-100-7 method) =3.555 min.; 185.7 (M+1 , 100 %) 187.7 (M+3, 97%).
  • 4
  • [ 68707-71-1 ]
  • (R)-4-nitrophenyl 4-((5-chlorothiophene-2-carboxamido)(cyclopropyl)methyl)piperidine-1-carboxylate [ No CAS ]
  • 2,3-dimethylpyridin-4-yl 4-[(R)-[(5-chlorothiophen-2-yl)formamido](cyclopropyl)methyl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.1% With dmap; sodium carbonate; In dimethyl sulfoxide; at 80℃; for 16.0h; To a suspension of <strong>[68707-71-1]2,3-dimethylpyridin-4-ol</strong> (46.5 mg, 0.377 mmol), DMAP (13.83 mg, 0.113 mmol) and Na2C03 (80 mg, 0.754 mmol) in Dimethyl Sulfoxide (DMSO) (3.0 ml_) was added 4-nitrophenyl (R)-4-((5-chlorothiophene-2- carboxamido)(cyclopropyl)methyl)piperidine-1 -carboxylate (35 mg, 0.075 mmol) and stirred at 80 C for 16h. Cooled to r.t., diluted with water, extracted with DCM, dried over sodium sulfate and concentrated. Purification by Gilson afforded the desired product as a solid (20.3 mg, 60.1 % yield). NMR (400 MHz, METHANOL-c/4) delta ppm 8.20 (d, J=5.3 Hz, 1 H) 7.58 (d, J=3.5 Hz, 1 H) 6.96 - 7.12 (m, 2 H) 4.28 - 4.42 (m, 1 H) 4.10 - 4.27 (m, 1 H) 3.01 - 3.22 (m, 2 H) 2.76 - 3.00 (m, 1 H) 2.51 (s, 3 H) 2.14 (s, 3 H) 2.08 (d, J= 13.1 Hz, 1 H) 1 .79 - 2.00 (m, 2 H) 1 .29 - 1 .51 (m, 2 H) 0.96 - 1 .12 (m, 1 H) 0.62 - 0.75 (m, 1 H) 0.42 - 0.52 (m, 1 H) 0.33 - 0.42 (m, 1 H) 0.19 - 0.31 (m, 1 H). LCMS (ESI) m/z calcd for C22H26CIN303S: 447.14 Found: 448.5 (M/M+1)+.
  • 5
  • [ 68707-71-1 ]
  • 4-nitrophenyl (S)-4-((4-chlorobenzamido)(phenyl)methyl)piperidine-1-carboxylate [ No CAS ]
  • 2,3-dimethylpyridin-4-yl 4-[(S)-[(4-chlorophenyl)formamido](phenyl)methyl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With caesium carbonate; In dimethyl sulfoxide; at 140℃; for 1.0h;Microwave irradiation; A mixture of 4-nitrophenyl (S)-4-((4-chlorobenzamido)(phenyl)methyl)piperidine-1 - carboxylate (100 mg, 0.20 mmol), <strong>[68707-71-1]2,3-dimethylpyridin-4-ol</strong> (170 mg, 1.40 mmol), Cs2C03(130 mg, 0.40 mmol) and DMSO (2.5 mL) was heated to 140C by microwave. After stirred at this temperature for 1 h, the reaction mixture was partitioned between EtOAc/hbO, and the layers were separated. The organic layer was washed with brine and dried over Na2S04. Solvent was removed under vacuum and the residue was purified by Gilson (C18, 10-50% MeCN in water with 0.1 % formic acid) to afford the title compound (73 mg, 77%) as a white solid.1H NMR (400 MHz, DMSO) delta 8.90 (d, J = 8.7 Hz, 1 H), 8.24 (d, J = 5.4 Hz, 1 H), 7.88 (d, J = 8.5 Hz, 2H), 7.54 (d, J = 8.5 Hz, 2H), 7.47 - 7.39 (m, 2H), 7.39 - 7.31 (m, 2H), 7.28 - 7.21 (m, 1 H), 7.02 (d, J = 5.4 Hz, 1 H), 4.81 (t, J = 8.8 Hz, 1 H), 4.24 - 3.93 (m, 2H), 3.03 - 2.79 (m, 2H), 2.46 (s, 3H), 2.11 - 1 .94 (m, 5H), 1 .36 - 1 .15 (m, 3H). LCMS (ESI) m/z calcd for C27H28CIN3O3: 477.18. Found: 478.23/480.29 (M/M+2)+.
  • 6
  • [ 68707-71-1 ]
  • 4-nitrophenyl (S)-4-((5-chlorothiophene-2-carboxamido)(phenyl)methyl)piperidine-1-carboxylate [ No CAS ]
  • (S)-2,3-dimethylpyridin-4-yl 4-((5-chlorothiophene-2-carboxamido)(phenyl)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With caesium carbonate; In dimethyl sulfoxide; at 140℃; for 1.0h;Microwave irradiation; A mixture of 4-nitrophenyl (S)-4-((5-chlorothiophene-2-carboxamido)(phenyl) methyl)piperidine-1 -carboxylate (110 mg, 0.22 mmol), 2,3-dimethylpyridin-3-ol (189 mg, 1 .54 mmol), Cs2C03(143 mg, 0.44 mmol) and DMSO (2.5 mL) was heated to 140C by microwave. After stirred at this temperature for 1 h, the reaction mixture was partitioned between EtOAc/H20, and the layers were separated. The organic layer was washed with brine and dried over Na2S04. Solvent was removed under vacuum and the residue was purified by Gilson (C18, 10-60% MeCN in water with 0.1 % formic acid) to afford the title compound (41 mg, 39% yield) as a white solid.1H NMR (400 MHz, DMSO) delta 8.88 (d, J = 8.6 Hz, 1 H), 8.26 (d, J = 5.5 Hz, 1 H), 7.81 (d, J = 4.0 Hz, 1 H), 7.44 - 7.31 (m, 4H), 7.29 - 7.23 (m, 1 H), 7.20 (d, J = 4.0 Hz, 1 H), 7.05 (d, J = 5.4 Hz, 1 H), 4.74 (t, J = 9.2 Hz, 1 H), 4.25 - 3.94 (m, 2H), 3.03 - 2.79 (m, 2H), 2.47 (s, 3H), 2.12 - 1 .94 (m, 5H), 1 .36 - 1 .15 (m, 3H). LCMS (ESI) m/z calcd for C25H26CIN3O3S: 483.14. Found: 484.07/486.26 (M/M+2)+.
 

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