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【结 构 式】

【分子编号】36674

【品名】2-ethyl-2,3-dihydro-1-benzofuran-2-carboxamide

【CA登记号】

【 分 子 式 】C11H13NO2

【 分 子 量 】191.22976

【元素组成】C 69.09% H 6.85% N 7.32% O 16.73%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

The condensation of 2-hydroxybenzaldehyde (I) with ethyl 2-bromobutyrate (II) by means of K2CO3 and NaI in DMF gives ethyl-2-(2-formylphenoxy) butyrate (III), which is reduced with NaBH4 and NaOEt in ethanol yielding the hydroxymethyl derivative (IV). The reaction of (IV) with SOCl2 affords the corresponding chloromethyl compound (V), which is cyclized by means of NaH in N-methylpyrrolidone to give 2-ethyl-2,3-dihydrobenzofuran-2-carboxylic acid ethyl ester (VI). The hydrolysis of the ethyl ester of (VI) with NaOH in methanol yields the expected carboxylic acid (VII), which is treated with SOCl2 and then with NH3 to afford the amide (VIII). This compound can also be obtained directly from ester (VI) by reaction with NH3. The dehydration of (VIII) by means of P2O5 or POCl3 gives the nitrile (IX), which is treated with HCl in ethanol yielding the carboxyimidate (X). Finally, this compound is cyclized with ethylenediamine (XI) in ethanol.

1 Edwards, C.R.; et al.; A practical synthesis of 2,3-dihydro-2-benzofurancarboxylic acid: A general route to 2,3-dihydrobenzofurans. J Heterocycl Chem 1987, 24, 495.
2 Chapleo, C.B.; et al.; alpha-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on alpha-adrenoreceptor activity. J Med Chem 1984, 27, 5, 570-6.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 21351 2-Hydroxybenzaldehyde;Salicylic aldehyde;2-Formylphenol;salicylaldehyde 90-02-8 C7H6O2 详情 详情
(II) 36668 ethyl 2-bromobutanoate 533-68-6 C6H11BrO2 详情 详情
(III) 36669 ethyl 2-(2-formylphenoxy)butanoate C13H16O4 详情 详情
(IV) 36670 ethyl 2-[2-(hydroxymethyl)phenoxy]butanoate C13H18O4 详情 详情
(V) 36671 ethyl 2-[2-(chloromethyl)phenoxy]butanoate C13H17ClO3 详情 详情
(VI) 36672 ethyl 2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylate C13H16O3 详情 详情
(VII) 36673 2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid C11H12O3 详情 详情
(VIII) 36674 2-ethyl-2,3-dihydro-1-benzofuran-2-carboxamide C11H13NO2 详情 详情
(IX) 36675 2-ethyl-2,3-dihydro-1-benzofuran-2-carbonitrile C11H11NO 详情 详情
(X) 36676 ethyl 2-ethyl-2,3-dihydro-1-benzofuran-2-carboximidoate C13H17NO2 详情 详情
(XI) 14754 ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine;1,2-Ethanediamine 107-15-3 C2H8N2 详情 详情
Extended Information