Sodium Hydroxide → 3-Amino-6-fluoro-2-(4-chlorophenyl)-4-quinolinecarboxylic acid

HRID 1073272

반응식

HRID 1073272 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-:13].[Na+].Cl.[NH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=O>O.C(O)C.O1CCCC1>[NH2:16][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[N:7][C:8]2[C:4]([C:5]=1[C:6]([OH:11])=[O:13])=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 2365665-FluoroisatinHCID 27982112-Amino-1-(4-chlorophenyl)ethan-1-one hydrochloride

생성물 1

HCID 150859693-Amino-6-fluoro-2-(4-chlorophenyl)-4-quinolinecarboxylic acid수율 95.3%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매3회HCID 8028Tetrahydrofuran용매

반응 조건

온도
85 °C

실험 절차

To a stirred suspension of 7 g of 5-fluoroisatin in 58 ml of water was added a solution of 9.36 g of sodium hydroxide in 33 ml of water. The solution was heated to 85° C. and a solution of 12 g of 2-amino-1-(4-chlorophenyl)ethanone hydrochloride in a mixture of 92 ml of ethanol and 40 ml of tetrahydrofuran and 92 ml of water was added drop-wise over 2 hours. After the addition was complete, the solution was refluxed for an additional 30 minutes and then the ethanol and tetrahydrofuran were removed by distillation. The mixture was cooled to 20° C. and filtered through celite. The filtrate was acidified to pH 4 with acetic acid. The solid was filtered off, washed with water and dried, giving 12.8 g of the desired compound as a yellow solid, mp 241°-243° C.

후처리

  1. additionwas added drop-wise over 2 hours
  2. additionAfter the addition
  3. temperaturethe solution was refluxed for an additional 30 minutes
  4. customthe ethanol and tetrahydrofuran were removed by distillation
  5. temperatureThe mixture was cooled to 20° C.
  6. filtrationfiltered through celite
  7. filtrationThe solid was filtered off
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-5dcee6d70101433ebcaa9e230850c4b0
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04968702

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