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Chemical Structure| 152815-18-4 Chemical Structure| 152815-18-4

Structure of 152815-18-4

Chemical Structure| 152815-18-4

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Product Details of [ 152815-18-4 ]

CAS No. :152815-18-4
Formula : C7H8ClNO
M.W : 157.60
SMILES Code : OCC1=CC(Cl)=NC(C)=C1
MDL No. :MFCD16607334

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Application In Synthesis of [ 152815-18-4 ]

* 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 [ 152815-18-4 ]

[ 152815-18-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 3998-88-7 ]
  • [ 152815-18-4 ]
YieldReaction ConditionsOperation in experiment
88% With acetic acid; In tetrahydrofuran; Lithium aluminium hydride (350 mg, 9.26 mmol) was added in portions to a solution of <strong>[3998-88-7]ethyl 2-chloro-6-methyl-4-pyridinecarboxylate</strong> (1.85 g, 9.26 mmol) in THF (40 ml) cooled at 0 C. The mixture was stirred for 15 minutes at 0 C. and acetic acid (2 ml) was added. The mixture was partitioned between ethyl acetate and water and the aqueous layer was adjusted to pH7.5 with 5 % aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with water and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (35/65) to give 2-chloro-4-hydroxymethyl-6-methylpyridine (1.28 g, 88%). 1 H NMR Spectrum: (CDCl3) 1.92(t, 1H); 2.53(s, 3H); 4.70(d, 2H); 7.06(s, 1H); 7.16(s, 1H) MS - ESI: 157 [MH]+ Elemental Analysis: Found C 53.1 H 5.3 N 8.7 C7 H8 NOCl Requires C 53.3 H 5.1 N 8.9%
  • 2
  • [ 152815-18-4 ]
  • [ 105250-16-6 ]
YieldReaction ConditionsOperation in experiment
88% In a variation of the above procedure, a solution of 2-chloro-6-methylpyridine-4-carboxylic, palladium (0.20 g, 10 mol % on carbon), ethyl acetate (45 mL), and triethylamine (2.8 mL, 20 mmol). The reaction mixture was placed under hydrogen at 1 atm for 21 hours. Additional Pearlman's catalyst (0.2 g) was added and the reaction was stirred under hydrogen for an additional 5 hours to effect dechlorination. The mixture was filtered through a pad of celite and concentrated. Purification by column chromatography (5:95 methanol:dichloromethane) gave (2-methyl-pyridin-4-yl)-methanol (1.48 g, 88%). The (2-methyl-pyridin-4-yl)-methanol was used to prepare 2-amino-3-(2-methyl-pyridin-4-yl)-propionitrile, from which 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-[cyano-(2-methyl-pyridin-4-ylmethyl)-methyl]-carbamoyl}-cyclohexyl)-amide was obtained (186 mg, 62%) in the manner described above. MS: 444 (M+H).
 

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