ChemicalBook CAS DataBase List methyl 4-[(hydroxyimino)methyl]-1-naphthalenecarboxylate

methyl 4-[(hydroxyimino)methyl]-1-naphthalenecarboxylate synthesis

6synthesis methods

Product Name:methyl 4-[(hydroxyimino)methyl]-1-naphthalenecarboxylate
CAS Number:943847-20-9
Molecular formula:C13H11NO3
Molecular Weight:229.23

62855-40-7 Synthesis

62855-40-7
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methyl 4-[(hydroxyimino)methyl]-1-naphthalenecarboxylate

943847-20-9
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Yield:943847-20-9 55%

Reaction Conditions:

with hydroxylamine hydrochloride in ethanol;water at 45; for 18 h;

Steps:

4

Preparation 4: (E/Z)-methyl 4-((hydroxyimino)methyl)-1-naphthoate To a solution of methyl 4-formyl-1-naphthoate (Preparation 3, 3.1 g, 14.5 mmol) in ethanol (125 mL) was added NH₂OH.NCl (2.05 g, 29 mmol) and water (20 mL). The solution was heated to 45° C. for 18 hours. The reaction was cooled and concentrated under vacuum to remove ethanol. Water (100 mL) was added to the residue and extracted with CH₂Cl₂(2×125 mL). The combined organic phases were dried (Na₂SO₄) and concentrated under vacuum. The crude intermediate was purified by chromatography on silica gel eluting from 100% heptane to 50:50 EtOAc:heptane to afford a solid (1.82 g, 55%). MS m/z (Cl) 230 [M+H]⁺.

References:

US2012/77765,2012,A1 Location in patent:Page/Page column 15

35615-97-5 Synthesis