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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
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HRID 1653682 반응식
[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
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반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-ce86b4407eed4039b5931cbb7ea0cb37
출처 데이터셋
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05403849

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