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Chemical Structure| 181473-92-7 Chemical Structure| 181473-92-7

Structure of 181473-92-7

Chemical Structure| 181473-92-7

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Product Details of [ 181473-92-7 ]

CAS No. :181473-92-7
Formula : C8H10ClNO
M.W : 171.62
SMILES Code : NCC1=CC(Cl)=CC=C1OC
MDL No. :MFCD03410973

Safety of [ 181473-92-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314-H335
Precautionary Statements:P260-P264-P270-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P405-P501
Class:8
UN#:2735
Packing Group:

Application In Synthesis of [ 181473-92-7 ]

* 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 [ 181473-92-7 ]

[ 181473-92-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 55877-79-7 ]
  • [ 181473-92-7 ]
YieldReaction ConditionsOperation in experiment
68% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 30℃; for 1.5h; Lithium aluminum hydride (0.34 g, 9 mmol) was added to a solution of <strong>[55877-79-7]5-chloro-2-methoxybenzonitrile</strong> (0.5 g, 3 mmol) in tetrahydrofuran (10 mL) at 0 C. The mixture was maintained at this temperature for a further 30 min and then stirred for an additional 1 h at 30 C. After cooling at 0 C, water (50 mL) was added and the amine was extracted twice with methylene chloride. The organic layers were dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The crude residue of the title compound (0.35 g, 68%) was used directly in the next step (synthesis of 9a and 9b). 1H NMR (DMSO-d6) δ 1.85 (bs, 2H, NH2), 3.64 (s, 2H, CH2), 3.77 (s, 1H, OCH3), 6.94 (d, J = 8.7 Hz, 1H, 3-H), 7.21 (dd, J = 8.7 Hz/2.7 Hz, 1H, 4-H), 7.38 (d, J = 2.7 Hz, 1H, 6-H); 13C NMR (DMSO-d6) δ 37.0 (CH2NH2), 56.0 (OCH3), 112.7 (C-3), 123.8 (C-5), 129.5 (C-4), 129.8 (C-6), 156.0 (C-2).
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 3h; A cooled (0 C) solution of 5-chloro-2-methoxy-benzonitrile (500 mg, 2.98 mmol) in THF (7.5 ml_) was added dropwise to a cooled solution of 2.4M UAIH4 solution in THF (1.86 ml_, 4.48 mmol) in THF (5.5ml_). The mixture was allowed to warm to room temperature and stirred for 3 h. The reaction was quenched by slow addition of water (0.25 ml_) followed by 4M NaOH (0.25 ml_). The mixture was filtered through Celite (filter material) rinsing through with with EtOAc (2 x 5 mL). The filtrate was concentrated in vacuo to afford the title compound as a yellow oil. (0518) LC-MS (Method B): Rt 2.43 min; MS m/z 171.7/173.7 = [M+H]+ (89% 215nm) (0519) 1 H NMR (500 MHz, DMSO-d6) d 7.38 (d, J = 2.7 Hz, 1 H), 7.21 (dd, J = 8.7, 2.7 Hz, 1 H), 6.94 (d, J = 8.7 Hz, 1 H), 3.77 (s, 3H), 3.64 (s, 2H), 1.89 (s (br), 2H).
 

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