2-Amino-4'-fluorobenzophenone → Methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate

HRID 23773

反応式

HRID 23773 の反応式
[CH:1]1([C:4](=O)[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.CS(O)(=O)=O.[NH2:16][C:17]1[CH:31]=[CH:30][CH:29]=[CH:28][C:18]=1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=O.NC1C=CC=CC=1C(C1C=CC(F)=CC=1)=O>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:18]3[C:17](=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:16]=2)[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 98372872-Amino-4'-fluorobenzophenone2 回HCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester3 回HCID 53446970(2-Aminophenyl)(4-fluorophenyl)methanone methanesulfonate

生成物 1

HCID 9901664Methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate収率 85.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

47.9 g of methyl 3-cyclopropyl-3-oxopropionate and 100 g of 2-amino-4′-fluorobenzophenone methanesulfonate were added to 584 g of toluene, and the mixture was dehydrated and refluxed at an internal temperature of 79 to 81° C. under a reduced pressure of 40 kPa. The reaction mixture was analyzed with HPLC during the reaction, and methyl 3-cyclopropyl-3-oxopropionate was added thereto by dividing it into several parts until the residual amount of 2-amino-4′-fluorobenzophenone was less than 2%. An additional amount of methyl 3-cyclopropyl-3-oxopropionate was 13.8 g. After 40 hours of reaction time, the residual amount of 2-amino-4′-fluorobenzophenone was 1.7%. The reaction solution was washed with 320 g of 4% aqueous solution of sodium hydroxide and then 140 g of 2% aqueous solution of sodium hydroxide. The reaction solution was further washed with 100 g of 5% brine solution, and then dried over 10 g of anhydrous magnesium sulfate. Toluene was removed under a reduced pressure, and crystallization was carried out in 740 g of cyclohexane to obtain 88.4 g of methyl 2-cyclopropyl-4-(4′-fluorophenyl)quinoline-3-carboxylate.

後処理

  1. additionwas added
  2. customAfter 40 hours of reaction time
  3. washThe reaction solution was washed with 320 g of 4% aqueous solution of sodium hydroxide
  4. washThe reaction solution was further washed with 100 g of 5% brine solution
  5. dry with materialdried over 10 g of anhydrous magnesium sulfate
  6. customToluene was removed under a reduced pressure, and crystallization

出典と根拠

ORDレコード
ord-b1e1809571ef406ca672f7ed096027c6
出典データセット
uspto-grants-2005_02
特許番号
US06852862B2

関連ノート

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