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

HRID 1653682Notes

Reaction equation

HRID 1653682 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Sources & evidence

ORD record
ord-ce86b4407eed4039b5931cbb7ea0cb37
Source dataset
uspto-grants-1995_04
Patent number
US05403849

Reaction notes

Loading…