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2-Methoxyethyl acetoacetate → Isopropyl 2-methoxyethyl 4-(3-amino-2-chloro-phenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate

HRID 1653682
ノート
印刷プレビュー

反応式

HRID 1653682 の反応式
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[CH:11]1[C:16]([C:17]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[O:18])=[C:15]([CH3:24])[NH:14][C:13]([CH3:25])=[C:12]1[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27].ClC1C([N+]([O-])=O)=CC=CC=1C=O.N/C(/C)=C\C(OC(C)C)=O.C(OCCOC)(=O)CC(C)=O>CC(O)C>[NH2:8][C:7]1[C:2]([Cl:1])=[C:3]([CH:11]2[C:16]([C:17]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[O:18])=[C:15]([CH3:24])[NH:14][C:13]([CH3:25])=[C:12]2[C:26]([O:28][CH:29]([CH3:30])[CH3:31])=[O:27])[CH:4]=[CH:5][CH:6]=1
参加物実験手順出典と根拠反応ノート

参加物

6

反応物 4

HCID 897342-Methoxyethyl acetoacetateHCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl esterHCID 126677132-Chloro-3-nitrobenzaldehydeHCID 67785793Isopropyl 2-methoxy-ethyl 4-(2-chloro-3-nitrophenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate

生成物 1

HCID 20080473Isopropyl 2-methoxyethyl 4-(3-amino-2-chloro-phenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

Isopropyl 2-methoxyethyl 4-(3-amino-2-chloro-phenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate ##STR31## 27.5 g (61 mmol, purity 96.5%) of isopropyl 2-methoxy-ethyl 4-(2-chloro-3-nitrophenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate, obtained by reaction of equimolar amounts of 2-chloro-3-nitrobenzaldehyde, isopropyl β-aminocrotonate and methoxyethyl acetoacetate in 2-propanol at the reflux temperature, are suspended in 500 ml of methanol and hydrogenated in the presence of Raney nickel (about 1.5 g, water-moist) under normal pressure and temperature until the end of the uptake of hydrogen (1 hour). The catalyst is filtered off and the residue obtained after concentration is purified by flash chromatography (toluene/ethyl acetate 1:0→5:1). Crystallization from toluene gives 24.0 g (93% of theory) of the title compound of melting point 118°-122° C.

出典と根拠

ORDレコード
ord-ce86b4407eed4039b5931cbb7ea0cb37
出典データセット
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05403849

反応ノート

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