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Diethyl Malonate → 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester

HRID 483290
ノート
印刷プレビュー

反応式

HRID 483290 の反応式
F[C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([OH:6])=O.[Na].[C:15](Cl)(=O)C(Cl)=O.[C:21]([O:29][CH2:30][CH3:31])(=[O:28])[CH2:22][C:23](OCC)=O.[Mg].[F:33][C:34]1[C:47]([F:48])=[C:46]([F:49])[C:45]([F:50])=[CH:44][C:35]=1[C:36]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:37].C(OC(OCC)OCC)C.C(OC(=O)C)(=O)C.[CH:68]1([NH2:71])[CH2:70][CH2:69]1>>[CH:68]1([N:71]2[C:2]3[C:3](=[CH:7][C:8]([F:13])=[C:9]([F:12])[C:10]=3[F:11])[C:4](=[O:6])[C:22]([C:21]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23]2)[CH2:70][CH2:69]1.[F:33][C:34]1[C:47]([F:48])=[C:46]([F:49])[C:45]([F:50])=[CH:44][C:35]=1[C:36]([C:38](=[CH:15][NH:71][CH:68]1[CH2:70][CH2:69]1)[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:37]
参加物実験手順後処理出典と根拠反応ノート

参加物

11

反応物 9

HCID 7761Diethyl MalonateHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 65578Oxalyl chlorideHCID 69828CyclopropylamineHCID 2975492,3,4,5-Tetrafluorobenzoic acid2 回HCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate
HCID 5360545
Sodium
HCID 5462224Magnesium

生成物 2

HCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 178471877HCID 178471877、化合物

実験手順

The starting materials for the present invention are known, or if new, may be prepared from known materials by known means. Thus, ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate is prepared as described in Belgian Pat. No. 899,399 or No. DE3318145. Alternatively, it may be prepared by a series of reactions starting from 2,3,4,5-tetrafluorobenzoic acid. The sodium salt of 2,3,4,5-tetrafluorobenzoic acid is reacted with oxalyl chloride and the product condensed with diethyl malonate in the presence of magnesium turnings to afford after hydrolysis 2,3,4,5-tetrafluorobenzoylacetic acid, ethyl ester. This compound is, in turn, treated with triethylorthoformate and acetic anhydride, followed by cyclopropylamine to afford 2-(2,3,4,5-tetrafluorobenzoyl)-3-cyclopropylamino acrylic acid, ethyl ester, which is then ring closed to give the desired starting material. The corresponding methyl ester is prepared using dimethylmalonate in the sequence described above.

後処理

  1. customif new, may be prepared
  2. customAlternatively, it may be prepared by a series of reactions
  3. customto afford

出典と根拠

ORDレコード
ord-3292f44d3208476cb08631810f010c12
出典データセット
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04578473

反応ノート

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