Salicylic Acid → 3-Chloro-N-(4-pyridinyl)-1H-indol-1-amine salicylate

HRID 1955671노트

반응식

HRID 1955671 반응식
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([NH2:11])[CH:3]=1.Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[C:20]([OH:29])(=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23]>CN1CCCC1=O.C(OCC)(=O)C>[C:20]([OH:29])(=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23].[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([NH:11][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:3]=1

참가 물질

6

반응물 3

HCID 338Salicylic AcidHCID 818524-Chloropyridine hydrochlorideHCID 9964198N-Amino-3-chloro-1H-indole

생성물 1

HCID 700281183-Chloro-N-(4-pyridinyl)-1H-indol-1-amine salicylate

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
60 °C

실험 절차

A suspension of crude 3-chloro-1H-indol-1-amine (65.5 g) and 4-chloropyridine hydrochloride (45 g) in 1-methyl-2-pyrrolidinone (250 ml) was stirred at 60° C. for eight hours. The cooled reaction mixture was quenched into 5% aqueous sodium hydroxide, extracted into toluene, dried and concentrated to give an oil. A portion of this oil was dissolved in ethyl acetate. Salicylic acid (1.2 eq) was added to precipitate the salt. The solid was collected at room temperature and dried. This solid was recrystallized with a charcoal treatment from methanol and oven dried (75° C., house vacuum) overnight to yield 10.9 g of the title compound as a solid, m.p. 185°-186° C. (dec.).

후처리

  1. customThe cooled reaction mixture
  2. customwas quenched into 5% aqueous sodium hydroxide
  3. extractionextracted into toluene
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil
  7. customto precipitate the salt
  8. customThe solid was collected at room temperature
  9. customdried
  10. customThis solid was recrystallized with a charcoal treatment from methanol and oven
  11. customdried (75° C., house vacuum) overnight

출처 및 근거

ORD 기록
ord-9c978422951b49fc94b95ff9711b848a
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05776955

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