Ethanol → 3-Amino-2-(1,1'-biphenyl)-4-yl-6-fluoro-4-quinolinecarboxylic acid

HRID 1073251노트

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HRID 1073251 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-].[Na+].Cl.[NH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)=O.C([OH:34])C>O.O1CCCC1>[NH2:16][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)=[N:7][C:8]2[C:4]([C:5]=1[C:6]([OH:11])=[O:34])=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2

참가 물질

7

반응물 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 2365665-Fluoroisatin2회HCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochloride

생성물 1

HCID 1314193-Amino-2-(1,1'-biphenyl)-4-yl-6-fluoro-4-quinolinecarboxylic acid

시약·촉매·용매 2

HCID 962Water용매3회HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

A 21.35 g portion of 5-fluoroisatin was suspended in 175 ml of water in a three-necked 2 liter flask equipped with a reflux condenser and addition funnel. To the suspension was added a solution of 28.5 g of sodium hydroxide in 100 ml of water, then the mixture was heated to 90° C. A solution of 44.08 g of 2-amino-4'-phenylacetophenone, hydrochloride in 550 ml of a 1:1 mixture of ethanol:water was warmed slightly, then 200 ml of tetrahydrofuran was added to effect dissolution. This solution was added dropwise to the hot solution of 5-fluoroisatin over 2.75 hours with vigorous stirring. When addition was complete the solution was stirred at 90° C. for 2 hours, then the organic solvents were removed by distillation at 85° C. The remaining solution was cooled, added to 1 liter of water and the red solids collected, washed with water and saved. The filtrate was acidified to pH 5 with glacial acetic acid and the resulting yellow solid collected, washed with water and saved. The red solids saved above were stirred in a mixture of 3 liters of water and 100 ml of ammoninum hydroxide for 1 hour, then filtered and the filtrate acidified to pH 5 with glacial acetic acid. The resulting yellow solid was collected, washed with water, combined with the yellow solid saved above and dried, giving 26.9 g of the desired product, mp 229°-232° 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. additionadded to 1 liter of water
  6. customthe red solids collected
  7. washwashed with water
  8. customthe resulting yellow solid collected
  9. washwashed with water
  10. stirringabove were stirred in a mixture of 3 liters of water and 100 ml of ammoninum hydroxide for 1 hour
  11. filtrationfiltered
  12. customThe resulting yellow solid was collected
  13. washwashed with water
  14. customdried

출처 및 근거

ORD 기록
ord-02d720bb922c4848b14e88e42be7100d
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04968702

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