Ethanol → 3-Amino-2-[1,1'-biphenyl]-4-yl-4-quinolinecarboxylic acid

HRID 1073252ノート

反応式

HRID 1073252 の反応式
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[OH-].[Na+].Cl.[NH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=O.C([OH:33])C>O.O1CCCC1>[NH2:15][C:16]1[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)=[N:1][C:11]2[C:6]([C:4]=1[C:2]([OH:33])=[O:3])=[CH:7][CH:8]=[CH:9][CH:10]=2

参加物

7

反応物 4

HCID 702EthanolHCID 7054Isatin2 回HCID 14798Sodium HydroxideHCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochloride

生成物 1

HCID 150859463-Amino-2-[1,1'-biphenyl]-4-yl-4-quinolinecarboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

A 4.42 g portion of isatin was suspended in 25 ml of water in a three-necked 1 liter flask equipped with a reflux condenser and addition funnel. To this suspension was added a solution of 6.4 g of sodium hydroxide in 20 ml of water, then the mixture was heated to 90° C. A solution of 15.0 g of 2-amino-4'-phenylacetophenone, hydrochloride in 300 ml of a 50:50 mixture of ethanol:water was warmed slightly, then 100 ml of tetrahydrofuran was added to effect dissolution. This solution was added dropwise to the hot solution of isatin over 1.5 hours with vigorous stirring. When addition was complete, the solution was stirred at 90° C. for 1 hour and then the organic solvents were removed by distillation at 85° C. The remaining solution was cooled, filtered and the filtrate acidified to pH 5 with glacial acetic acid. The resulting solid was collected, washed with water and dried. The yellow solids were suspended in 40 ml of ethanol, filtered and dried, giving 2.19 g of the desired product, mp 223°-225° C. (dec.).

後処理

  1. customequipped with a reflux condenser and addition funnel
  2. additionWhen addition
  3. customthe organic solvents were removed by distillation at 85° C
  4. temperatureThe remaining solution was cooled
  5. filtrationfiltered
  6. customThe resulting solid was collected
  7. washwashed with water
  8. customdried
  9. filtrationfiltered
  10. customdried

出典と根拠

ORDレコード
ord-208b9e45d46c47eab15f040892b6d5ef
出典データセット
uspto-grants-1990_11
特許番号
US04968702

反応ノート

読み込み中…