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Chemical Structure| 4377-33-7 Chemical Structure| 4377-33-7

Structure of 4377-33-7

Chemical Structure| 4377-33-7

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Product Details of [ 4377-33-7 ]

CAS No. :4377-33-7
Formula : C6H6ClN
M.W : 127.57
SMILES Code : ClCC1=NC=CC=C1
MDL No. :MFCD05861645
InChI Key :NJWIMFZLESWFIM-UHFFFAOYSA-N
Pubchem ID :23393

Safety of [ 4377-33-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P261-P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 4377-33-7 ]

* 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.

  • Upstream synthesis route of [ 4377-33-7 ]
  • Downstream synthetic route of [ 4377-33-7 ]

[ 4377-33-7 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 4377-33-7 ]
  • [ 619-08-9 ]
  • [ 179687-79-7 ]
YieldReaction ConditionsOperation in experiment
52% With hydrogenchloride; caesium carbonate; sodium iodide In acetonitrile at 60℃; for 5 h; Example 71; 4-f [3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino) [1]benzothieno[2,3-d] pyrimidin-7-ol; Step 1. Preparation of 3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamine; EPO <DP n="84"/> 2-chloro-4-nitro phenol (10 g, 57.6 mmol, 1 equiv), 2-pycolyl chloride hydrogen chloride (9.45 g, 57.6 mmol, 1 equiv) cesium carbonate 41.3 (126.8 mmol, 2.2 equiv) and sodium iodide (8.64 g, 57.6 mmol, 1 equiv) were suspended in 200 mL acetonitrile. The reaction mixture was stirred at 60°C for 5h. The resulted suspension was filtered and washed with water (400 mL), yielding 2-(2-chloro-4- nitro-phenoxymethyl)-pyridine (8 g, 52percent) as a red solid.2-(2-chloro-4-nitro-phenoxyrnethyl)-pyridine (8 g, 30.2mmol, 1 equiv) and iron (8.44 g, 151.1 mmol, 5 equiv) were mixed in acetic acid (100 mL ) and EtOAc (50 mL ) and were stirred at rt overnight. The reaction mixture was filtered through a pad of Celite.(R).. The filtrate was concentrated in vacuo and neutralized with saturated Na2CO3 solution. The solution was extracted with EtOAc and the organic layer was washed with brine and concentrated in vacuo. The resulting crude material was purified by flash chromatography eluting with EtOAc/hexane (3:7) to give 3-Chloro- 4-(pyridin-2-ylmethoxy)-phenylamine (3.2 g, 52percent) as a white solid. 1H-NMR (CDCl3) δ 5.18 (s, 2H), 6.50 (dd, 1H), 6.76 (d, 1H),. 6.80 (d, 1H), 7.22 (m, 1H), 7.64 (d, 1H), 7.73 (td, 1H), 8.55 (m, 1H); LCMS RT = 0.89 min, [M+H]+ = 235.1.
References: [1] Patent: WO2006/44524, 2006, A1, . Location in patent: Page/Page column 82-83.
[2] European Journal of Medicinal Chemistry, 2018, vol. 144, p. 330 - 348.
 

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