Acetic Acid → 1-Cyclopropyl-8-(difluoromethoxy)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1461027

反応式

HRID 1461027 の反応式
C(O)(=O)C.S(=O)(=O)(O)O.[CH:10]1([N:13]2[C:22]3[C:17](=[CH:18][C:19]([F:28])=[C:20]([F:27])[C:21]=3[O:23][CH:24]([F:26])[F:25])[C:16](=[O:29])[C:15]([C:30]([O:32]CC)=[O:31])=[CH:14]2)[CH2:12][CH2:11]1>O>[CH:10]1([N:13]2[C:22]3[C:17](=[CH:18][C:19]([F:28])=[C:20]([F:27])[C:21]=3[O:23][CH:24]([F:25])[F:26])[C:16](=[O:29])[C:15]([C:30]([OH:32])=[O:31])=[CH:14]2)[CH2:11][CH2:12]1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 15023786Ethyl 1-cyclopropyl-8-(difluoromethoxy)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

生成物 1

HCID 150237871-Cyclopropyl-8-(difluoromethoxy)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid収率 84.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

9 ml of acetic acid, 1.2 ml of concentrated sulfuric acid and 7 ml of water were added to 1.40 g (0.0039 moles) of ethyl 1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate [(XX), R1 =--OCHF2, R3' =H, R17 =C2H5, X=F] (prepared as described in Preparation 6), and the mixture was heated under reflux for 1 hour. At the end of this time, it was cooled to room temperature and poured into ice-water. The precipitated crystals were collected by filtration and washed with water and with diethyl ether, in that order, to give 1.09 g of 1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as colorless needles, melting at 202°-207° C.

後処理

  1. custom' =H, R17 =C2H5, X=F] (prepared as described in Preparation 6)
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with water and with diethyl ether, in that order

出典と根拠

ORDレコード
ord-c95dbf359bad451ab847eab5058ce056
出典データセット
uspto-grants-1991_12
特許番号
US05073556

関連ノート

読み込み中…