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Sodium Hydroxide → 3-Amino-6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-4-quinolinecarboxylic acid

HRID 1073263
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HRID 1073263 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]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])=[CH:22][CH:21]=1)=O>O.C(O)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][C:27]=3[F:32])=[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 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 2365665-FluoroisatinHCID 221583512-Amino-1-(2'-fluoro[1,1'-biphenyl]-4-yl)-ethanone hydrochloride

생성물 1

HCID 150859603-Amino-6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-4-quinolinecarboxylic acid수율 79.1%

시약·촉매·용매 3

HCID 962Water용매2회
HCID 8028
Tetrahydrofuran
용매
HCID 19096565Water ethanol용매

실험 절차

To a stirred suspension of 4.13 g of 5-fluoroisatin in 40 ml of water was added a solution of 5.62 g of sodium hydroxide in 20 ml of water. This mixture was heated to 85°-90° C. and a warm solution of 9.3 g of 2-amino-1 (2'-fluoro[1,1'-biphenyl]-4-yl)ethanone, hydrochloride in 140 ml of ethanol:water (1:1) and 30 ml of tetrahydrofuran was added dropwise over 2 hours. This mixture was stirred at reflux for 2 hours, then the ethanol was distilled off. The reaction was filtered and the filtrate acidified to pH 4-5 with acetic acid. The resulting solid was collected, washed with water and crystallized from 400 ml of hot ethanol, giving 7.45 g of the desired product as a yellow solid, mp 248°-250° C.

후처리

  1. temperatureThis mixture was heated to 85°-90° C.
  2. temperatureat reflux for 2 hours
  3. distillationthe ethanol was distilled off
  4. filtrationThe reaction was filtered
  5. customThe resulting solid was collected
  6. washwashed with water
  7. customcrystallized from 400 ml of hot ethanol

출처 및 근거

ORD 기록
ord-95395aac5bb04592a69a49f71bcafa53
출처 데이터셋
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04968702

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