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Hydrochloric Acid → 2-(4-Isopropylthiazol-2-YL)-7-methoxy-8-methylquinolin-4-OL

HRID 402143
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인쇄 미리보기

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HRID 402143 반응식
CC(C)([O-])C.[K+].[CH:7]([C:10]1[N:11]=[C:12]([C:15]([NH:17][C:18]2[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[CH:21]=[CH:20][C:19]=2[C:27](=[O:29])[CH3:28])=O)[S:13][CH:14]=1)([CH3:9])[CH3:8].O.Cl>C(O)(C)(C)C.CCOCC>[OH:29][C:27]1[C:19]2[C:18](=[C:23]([CH3:24])[C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:17]=[C:15]([C:12]2[S:13][CH:14]=[C:10]([CH:7]([CH3:9])[CH3:8])[N:11]=2)[CH:28]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 53482122N-(6-Acetyl-3-methoxy-2-methylphenyl)-4-(propan-2-yl)-1,3-thiazole-2-carboxamide

생성물 1

HCID 1784876922-(4-Isopropylthiazol-2-YL)-7-methoxy-8-methylquinolin-4-OL수율 89.2%

시약·촉매·용매 2

HCID 3283
Diethyl Ether
용매
HCID 6386tert-Butanol용매

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온도
100 °C

실험 절차

Potassium tert-butoxide (21.8 g, 195 mmol) was added to a suspension of 2′-[[(4-iso-propylthiazole-2-yl)(oxo)methyl]amino]-4′-methoxy-3′-methylacetophenone (35, 30.8 g, 92.7 mmol) in tert-butanol. The resulting reaction mixtures was heated at 100° C. overnight. Then, the reaction mixture was cooled at room temperature and diluted with ether (100 mL). The precipitate was filtered off and washed with Et2O to give a powder (fraction A). The mother liquor was concentrated in vacuo, triturated in ether, filtered off, and washed with ether to give a powder (fraction 2). Fractions 1 and 2 were mixed and poured into water (250 mL). The pH of the resulting solution was adjusted to 6-7 (control with pH paper) with HCl 1N. The precipitate was filtered off, washed with water and dried. Then, the solid was triturated in diisopropyl ether, filtered off and dried to give 26 g (88%) of the title product 36 as a brownish solid: m/z=315 (M+H)+.

후처리

  1. customThe resulting reaction mixtures
  2. temperatureThen, the reaction mixture was cooled at room temperature
  3. filtrationThe precipitate was filtered off
  4. washwashed with Et2O
  5. customto give a powder (fraction A)
  6. concentrationThe mother liquor was concentrated in vacuo
  7. customtriturated in ether
  8. filtrationfiltered off
  9. washwashed with ether
  10. customto give a powder (fraction 2)
  11. additionFractions 1 and 2 were mixed
  12. filtrationThe precipitate was filtered off
  13. washwashed with water
  14. customdried
  15. customThen, the solid was triturated in diisopropyl ether
  16. filtrationfiltered off
  17. customdried

출처 및 근거

ORD 기록
ord-268ef13a51d3474d9fe38f5035fb3306
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08741926B2

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