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

HRID 1073252노트

반응식

HRID 1073252 반응식
[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

참가 물질

7

반응물 4

HCID 702EthanolHCID 7054Isatin2회HCID 14798Sodium HydroxideHCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochloride

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매3회HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-208b9e45d46c47eab15f040892b6d5ef
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04968702

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