3,4-Diaminobenzoic acid → 2,3-Bis(4-methoxyphenyl)quinoxaline-6-carboxylic acid

HRID 396864

反応式

HRID 396864 の反応式
Cl.Cl.NC1C=C(C2C(C3C=CC(O)=C(N)C=3)=NC3C(=CC=C(C(O)=O)C=3)N=2)C=CC=1O.[NH2:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[NH2:42])[C:36]([OH:38])=[O:37].[CH3:43][O:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]([C:53]([C:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=2)=O)=O)=[CH:47][CH:46]=1>>[CH3:62][O:61][C:58]1[CH:57]=[CH:56][C:55]([C:53]2[C:51]([C:48]3[CH:47]=[CH:46][C:45]([O:44][CH3:43])=[CH:50][CH:49]=3)=[N:32][C:33]3[C:41](=[CH:40][CH:39]=[C:35]([C:36]([OH:38])=[O:37])[CH:34]=3)[N:42]=2)=[CH:60][CH:59]=1

参加物

4

反応物 3

HCID 692633,4-Diaminobenzoic acidHCID 710434,4'-DimethoxybenzilHCID 1363883402,3-Bis(3-amino-4-hydroxyphenyl)quinoxaline-6-carboxylic acid dihydrochloride

生成物 1

HCID 9803122,3-Bis(4-methoxyphenyl)quinoxaline-6-carboxylic acid

実験手順

Briefly, the AB2 monomer, 2,3-bis(3-amino-4-hydroxyphenyl)quinoxaline-6-carboxylic acid dihydrochloride, is synthesized by condensing 3,4-diaminobenzoic acid and 4,4′-dimethoxybenzil to afford 2,3-bis(4-methoxyphenyl) quinoxaline-6-carboxylic acid, followed by demethylation in hydrobromic acid in acetic acid to form 2,3-bis(4-hydroxyphenyl) quinoxaline-6-carboxylic acid. The latter is then nitrated using nitric acid (70% conc.) in acetic acid at room temperature, yielding 2,3-bis(3-nitro-4-hydroxyphenyl) quinoxaline-6-carboxylic acid. The desired monomer is prepared by catalytic reduction in the presence of palladium catalyst in 10% hydrochloric acid.

出典と根拠

ORDレコード
ord-b173923705b04832a408af0aacc722cf
出典データセット
uspto-grants-2003_08
特許番号
US06608171B1

関連ノート

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