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Chemistry
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(2-(Aminomethyl)-5-chlorophenyl)methanol
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[ CAS No. 439117-39-2 ] {[proInfo.proName]}

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Chemical Structure| 439117-39-2
Chemical Structure| 439117-39-2
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Product Details of [ 439117-39-2 ]

CAS No. :439117-39-2 MDL No. :MFCD09038055
Formula : C8H10ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 171.62 Pubchem ID :-
Synonyms :

Safety of [ 439117-39-2 ]

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Precautionary Statements: UN#:
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Application In Synthesis of [ 439117-39-2 ]

* 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 [ 439117-39-2 ]

[ 439117-39-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 439117-38-1 ]
  • [ 58083-59-3 ]
  • [ 439117-39-2 ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 3620 - 3627
  • 2
  • [ 439117-38-1 ]
  • [ 439117-39-2 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In tetrahydrofuran; Step C. [2-(aminomethyl)-5-chlorophenyl]methanol To LAH (1 M/Et2O, 104.4 ml, 104.4 mmol) in anhydrous THF (300 ml) at0 C. was added <strong>[439117-38-1]methyl 5-chloro-2-cyanobenzoate</strong> (9.28 g, 0.512 mmol) maintaining the temperature below 20 C. After one half hour, quenched at 0 C. with water (3.97 ml), NaOH (1N, 11.9 ml, 11.9 mmol) and water (3.97 ml). A precipitate was filtered out and washed with THF. The filtrate was concentrated in vacuo and was used immediately in the next step. H NMR (CDCl3, 400 MHz): delta7.17-7.36 (m, 3 H); 4.60 (s, 2 H); 3.98 (s, 2 H);
In tetrahydrofuran; water; Step.3 2-aminomethyl-5-chlorobenzyl alcohol To a stirred solution of lithium aluminum hydride (104 mL of a 1.0 molar solution in ether, 104 mmol) in anhydrous THF (200 mL) at 0 C. was added <strong>[439117-38-1]methyl 5-chloro-2-cyanobenzoate</strong> (9.28 g, 47 mmol) in anhydrous THF (15 mL). After 1 h, the reaction was quenched at 0 C. with water (3.9 mL), 3.0 N aqueous NaOH (4.0 mL, 12 mmol) and water (3.9 mL). Ether (200 mL) was added and the thick precipitate which had formed was removed by filtration and washed with THF. The filtrate was concentrated in vacuo and the crude product, 2-aminomethyl-5-chlorobenzyl alcohol, was used immediately in the next step. 1H NMR (CDCl3, 400 MHz) 7.17-7.36 ppm (m, 3H); 4.60 ppm (s, 2H); 3.98 ppm (s, 2H).
With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 20℃; for 0.5h; Step C: Preparation of 2-(aminomethyl)-5-chlorophenyl]methanol To LAH (1 M/Et20, 104.4 ml, 104.4 mmol) in anhydrous THF (300 ml) at 0C was added <strong>[439117-38-1]methyl 5-chloro-2-cyanobenzoate</strong> (9.28g, 0.512 mmol) maintaining the temperature below 20 C. After one half hour, quenched at 0C with water (3.97 ml), NaOH (IN, 11.9 ml, 11.9 mmol) and water (3.97 ml). A precipitate was filtered out and washed with THF. The filtrate was concentrated in vacuo and was used immediately in the next step. H NMR (CDCI3, 400 MHz): delta 7.17-7.36 (m, 3 H); 4.60 (s, 2 H); 3.98 (s, 2 H);
In tetrahydrofuran; water; Step. 3 To a stirred solution of lithium aluminum hydride (104 mL of a 1.0 molar solution in ether, 104 mmol) in anhydrous THF (200 mL) at 0 C. was added <strong>[439117-38-1]methyl 5-chloro-2-cyanobenzoate</strong> from the previous step (9.28 g, 47 mmol) in anhydrous THF (15 mL). After 1 h, the reaction was quenched at 0 C with water (3.9 mL), 3.0 N aqueous NaOH (4.0 mL, 12 mmol) and water (3.9 mL). Ether (200 mL) was added and the thick precipitate which had formed was removed by filtration and washed with THF. The filtrate was concentrated in vacuo and the crude product, 2-aminomethyl-5-chlorobenzyl alcohol, was used immediately in the next step. 1H NMR (CDCl3, 400 MHz) 7.17-7.36 ppm (m, 3H); 4.60 ppm (s, 2H); 3.98 ppm (s, 2H).

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 3620 - 3627
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4161 - 4164
[3]Patent: US2002/193398,2002,A1
[4]Patent: US6528503,2003,B2
[5]Patent: WO2014/25658,2014,A1 .Location in patent: Page/Page column 25
[6]Patent: US2002/119992,2002,A1
  • 3
  • [ 21739-93-5 ]
  • [ 439117-39-2 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3477 - 3482
[2]Patent: WO2014/25658,2014,A1
[3]Patent: US2002/119992,2002,A1
  • 4
  • [ 56961-26-3 ]
  • [ 439117-39-2 ]
Reference： [1]Patent: US2002/119992,2002,A1

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