Sodium Hydroxide → 3-Amino-2-[1,1'-biphenyl]-4-yl-6,8-dichloro-4-quinolinecarboxylic acid

HRID 1073260

반응식

HRID 1073260 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6](=[O:12])[C:5]2=O.[OH-:14].[Na+].Cl.[NH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)=O>O.C(O)C.O.O1CCCC1>[NH2:17][C:18]1[C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)=[N:7][C:8]2[C:4]([C:5]=1[C:6]([OH:12])=[O:14])=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=2[Cl:11]

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 807715,7-Dichloro-1H-indole-2,3-dione2회HCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochloride

생성물 1

HCID 150859543-Amino-2-[1,1'-biphenyl]-4-yl-6,8-dichloro-4-quinolinecarboxylic acid

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매HCID 19096565Water ethanol용매

반응 조건

온도
90 °C

실험 절차

A 3.02 g portion of 5,7-dichloroisatin was suspended in 25 ml of water in a 500 ml three-necked flask. A solution of 3.96 g of sodium hydroxide in 15 ml of water was added and the mixture heated to 90° C. A 6.0 g portion of 2-amino-4'-phenylacetophenone hydrochloride was dissolved in a mixture of 80 ml of absolute ethanol:water (1:1) and 20 ml of tetrahydrofuran. This solution was kept warm and with stirring, added dropwise to the 5,7-dichloroisatin solution over 1.5 hours. The resulting solution was refluxed 1.5 hours, then the solvent was distilled off at 85° C. The red solids were collected and washed with 50 ml of water. These solids were then stirred in 1800 ml of water, filtered and the filtrate acidified to pH 5 with glacial acetic acid. The resulting orange solids were collected and dried, giving 3.25 g of the desired product, mp 244°-245° C.

후처리

  1. temperatureThis solution was kept warm
  2. temperatureThe resulting solution was refluxed 1.5 hours
  3. distillationthe solvent was distilled off at 85° C
  4. customThe red solids were collected
  5. washwashed with 50 ml of water
  6. stirringThese solids were then stirred in 1800 ml of water
  7. filtrationfiltered
  8. customThe resulting orange solids were collected
  9. customdried

출처 및 근거

ORD 기록
ord-4a06145db81d475e8aa07e4e275fb0b4
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04968702

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