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Chemical Structure| 1386986-06-6 Chemical Structure| 1386986-06-6

Structure of 1386986-06-6

Chemical Structure| 1386986-06-6

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Product Details of [ 1386986-06-6 ]

CAS No. :1386986-06-6
Formula : C8H7ClN2O
M.W : 182.61
SMILES Code : N#CC1=NC=C(Cl)C=C1COC
English Name :5-Chloro-3-(methoxymethyl)picolinonitrile
MDL No. :MFCD23163215
InChI Key :AHIYBRIEVPKSGH-UHFFFAOYSA-N
Pubchem ID :68109909

Safety of [ 1386986-06-6 ]

Application In Synthesis of [ 1386986-06-6 ]

* 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 [ 1386986-06-6 ]

[ 1386986-06-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 770697-94-4 ]
  • [ 1386986-05-5 ]
  • [ 1386986-06-6 ]
YieldReaction ConditionsOperation in experiment
With zinc In N,N-dimethyl-formamide at 150℃; for 2h; Inert atmosphere; 1.c c) 5-Chloro-3-methoxymethyl-pyridine-2-carbonitrile; To a mixture of 2,5-dichloro-3-methoxymethyl-pyridine (1150 mg, 5.99 mmol) zinc cyanide (492 mg, 4.19 mmol) and zinc dust (39.2 mg, 0.599 mmol) in dry DMF (18 ml) was added (dppf)PdCI2 CH2CI2 adduct catalyst (245 mg, 0.299 mmol) under nitrogen. The mixture was heated at 150 °C for 2 hours. After 2 h the starting material was consumed and the reaction mixture was diluted with ethyl acetate and washed with saturated bicarbonate solution and brine, dried over sodium sulfate, filtered and evaporated. The crude dark residue (960 mg) was chromatographed over silica gel (cyclohexane:ethyl acetate 80:20) to provide the title compound as a yellow solid.TLC: Rf=0.41 (3: 1 cyclohexane: ethyl acetate);LC-MS: RtH9= 0.83 min. (100 % pure, ESI+ 183, 185); H-NMR (360 MHz, CDCI3): δ 8.56 (d, 1 H, H6), 7.95 (d, 1 H, H4), 4.66 (s, 2H), 3.51 (s, 3H).
  • 2
  • [ 176433-49-1 ]
  • [ 1386986-06-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ethanol; sodium tetrahydroborate / 1 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 2.2: 20 °C 3.1: zinc / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 2 h / 150 °C / Inert atmosphere
  • 3
  • [ 558465-93-3 ]
  • [ 1386986-06-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 1.2: 20 °C 2.1: zinc / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 2 h / 150 °C / Inert atmosphere
  • 4
  • [ 1386986-06-6 ]
  • [ 1386986-57-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-chloro-3-methoxymethyl-pyridine-2-carbonitrile With water; sodium hydroxide at 100℃; for 4h; Stage #2: With hydrogenchloride In water 1.d d) 5-Chloro-3-methoxymethyl-pyridine-2-carboxylic acid; A suspension of 5-chloro-3-methoxymethyl-pyridine-2-carbonitrile (100 mg, 0.548 mmol) in 2N NaOH (2 ml) was stirred at 100° C for 4 hours. The reaction mixture was washed with diethyl ether and then set acidic (pH 5-6) with 2M HCI. The aqueous layer was extracted with ethyl acetate and the organic phase washed with brine, dried over sodium sulfate, filtered and evaporated to provide the title compound as white solid.MS: ESI- 200; LC-MS: RtH9= 0.58 min. (100 % pure, ESI+ 202);1 H-NMR (360 MHz, CDCI3): δ 11.1 (s, broad, 1 H, COOH), 8.45 (d, 1 H, H6), 8.25 (d, 1 H, H4), 4.99 (s, 2H), 3.55 (s, 3H).
  • 5
  • [ 1386986-06-6 ]
  • [ 1386984-01-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 4 h / 100 °C 1.2: pH 5 - 6 2.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 20 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 18 h / 20 °C 3.2: Cooling with ice
  • 6
  • [ 1386986-06-6 ]
  • [ 1386985-56-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 4 h / 100 °C 1.2: pH 5 - 6 2.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 20 h / 20 °C
 

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Technical Information

Categories

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[ 1386986-06-6 ]

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Related Parent Nucleus of
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