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Methyl acetoacetate → Ammonia
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Methyl acetoacetate | HCID 7757 | — |
| 反応物 | Piperidine | HCID 8082 | — |
| 反応物 | 2,1,3-Benzoxadiazole-4-carbaldehyde | HCID 10290873 | — |
| 反応物 | 3-Aminocrotonic acid-(2-dimethylaminoethyl)ester | HCID 12529187 | — |
| 反応物 | 2-Acetyl-3-benzofurazan-4-yl-acrylic acid methyl ester | HCID 53433213 | — |
| 溶媒 | Acetic Acid | HCID 176 | — |
| 溶媒 | Benzene | HCID 241 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | Ammonia | HCID 222 | — |
| 生成物 | 2-(Dimethylamino)ethyl 3-oxobutanoate | HCID 12529170 | — |
反応手順
2,1,3-Benzoxadiazol-4-carbaldehyde is reacted with aceto-acetic acid methyl ester in benzene in the presence of catalytic amounts of piperidine and acetic acid. The resultant 2-acetyl-3-(2,1,3-benzoxadiazol-4-yl)-2-propenoic acid methyl ester (crystalline, mixture of Z and E isomers) is cyclized in dioxane under refluxing with an equivalent amount of 3-aminocrotonic acid-(2-dimethylaminoethyl)ester {M.P. 56°; obtained by reaction of aceto-acetic acid-(2-dimethylaminoetyl)ester [B.P.0.01 mm 140°-150°, obtained by reaction of diketen with 2-dimethylaminoethanol at 70°], with ammonia gas at 60°}, to give 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-3-pyridine carboxylic acid-(2-dimethylaminoethyl)ester (M.P. 161°).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US04707482 |
| 出典データセット | uspto-grants-1987_11 |
| ORD ID | ord-f29eca7ed8a44004bccdb125e00b9758 |
| 出典メモ | uspto-grants-1987_11 |