ChemicalBook CAS DataBase List 1-Methyl-aminomethyl naphthalene

1-Methyl-aminomethyl naphthalene synthesis

13synthesis methods

Product Name:1-Methyl-aminomethyl naphthalene
CAS Number:14489-75-9
Molecular formula:C12H13N
Molecular Weight:171.24

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14489-75-9
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Yield:14489-75-9 97%

Reaction Conditions:

Stage #1: N-methyl-1-naphthalenecarboxamidewith lithium aluminium tetrahydride in tetrahydrofuran at 0;Heating / reflux;
Stage #2: with water;ammonium chloride in tetrahydrofuran at 0 - 20; for 1 h;

Steps:

1.8

A solution of naphthalene- 1-carboxylic acid methyl amide (0.83 g, 4.40 mmol) in anhydrous tetrahydrofuran (10 mL) was added via a syringe to a stirred suspension of lithium aluminum hydride (0.41 g, 9.68 mmol) in anhydrous tetrahydrofuran (10 mL), at O⁰C, over 10 minutes under nitrogen. The mixture was heated to reflux overnight, cooled to O⁰C and quenched with saturated ammonium chloride solution (2 mL). The reaction was allowed to warm to ambient temperature over 1 hour, filtered through a pad of celite, extracted with ether, and the organic layer was dried and concentrated under reduced pressure to give the title compound as a yellow oil (0.75 g, 97%). The material is used directly in the next step without purification. ¹H-NMR (CDCl₃) δ: 7.40-7.57 (m, 4H), 7.78 (m, IH), 7.87(m, IH), 8.12 (m, IH).

References:

WO2008/73863,2008,A2 Location in patent:Page/Page column 64