4-Chloro-3-nitroanisole → Diethyl (4-methoxy-2-nitrophenyl)malonate

HRID 1914674Notes

Reaction equation

HRID 1914674 reaction equation
NC1C=[C:6]([O:8]C)[CH:5]=CC=1CCO.ClC1C=C[C:17]([O:20]C)=[CH:16]C=1[N+]([O-])=O.NC1C=C(OC)C=CC=1C(CO)CO.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([CH:47]([CH2:50][OH:51])[CH2:48][OH:49])=[C:43]([N+:52]([O-:54])=[O:53])[CH:42]=1>>[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([CH:47]([C:48]([O:20][CH2:17][CH3:16])=[O:49])[C:50]([O:8][CH2:6][CH3:5])=[O:51])=[C:43]([N+:52]([O-:54])=[O:53])[CH:42]=1

Participants

5

Reactant 4

HCID 251404-Chloro-3-nitroanisoleHCID 131958022-(4-Methoxy-2-nitrophenyl)propane-1,3-diolHCID 593529832-(2-Amino-4-methoxyphenyl)propane-1,3-diolHCID 593529932-(2-Amino-4-methoxyphenyl)ethanol

Product 1

HCID 1811374Diethyl (4-methoxy-2-nitrophenyl)malonate

Procedure

In particular, 2-(2-amino-4-methoxyphenyl)ethanol may be prepared from 1-chloro-4-methoxy-2-nitrobenzene using conventional procedures, known by one skilled in the art and described in the literature (Bioorg. Med. Chem, 2004). Similarly, 2-(2-amino-4-methoxyphenyl)propane-1,3-diol may be prepared by hydrogenation of 2-(4-methoxy-2-nitrophenyl)propane-1,3-diol obtained by reduction of diethyl (4-methoxy-2-nitrophenyl)malonate. Also, 5-methoxy-2-(2-methoxyethyl)aniline may be prepared by reduction of the product resulting from the methylation of 2-(4-methoxy-2-nitrophenyl)ethanol. 5-Methoxy-2-[2-(methylsulfonyl)ethyl]aniline may be prepared by hydrogenation of the product resulting from the oxidation of 4-methoxy-1-[2-(methylthio)ethyl]-2-nitrobenzene. The latter may be prepared by reaction between sodium thiomethoxide and the intermediate obtained by bromo-de-hydroxylation of 2-(4-methoxy-2-nitrophenyl)ethanol as described in the scheme below.

Sources & evidence

ORD record
ord-5103928249d841009b462c1cd13fad59
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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