Triethylamine → 3-Bromo-7-chloro-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine

HRID 1252408노트

반응식

HRID 1252408 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C:14]3([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Br:21]Br.[OH-].[Na+].C(N(CC)CC)C>C(O)(=O)C.O>[Br:21][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:12][CH2:13][C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24408BromineHCID 142092337-Chloro-N-[(1-hydroxycyclohexyl)methyl]-4-quinolinamine

생성물 1

HCID 142092443-Bromo-7-chloro-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine수율 49.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

A solution of 11.2 g of 7-chloro-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine in 130 ml of glacial acetic acid was stirred at room temperature and 6.15 g of bromine was added dropwise. The product precipitated from the solution as the hydrobromide salt and was isolated by filtration. The solid was then suspended in water and basified with sodium hydroxide. After two hours of stirring, the solid was collected by filtration. By combustion analysis, the product proved to be a hemi-hydrobromide salt, and therefore, it was necessary to dissolve the solid in methanol and 1 equivalent of trietylamine with heating. A solid resulted which was recrystallized from ethanol to give 7 g of crystalline solid with a melting point of 151°-154° C.

후처리

  1. customThe product precipitated from the solution as the hydrobromide salt
  2. customwas isolated by filtration
  3. filtrationthe solid was collected by filtration
  4. dissolutionto dissolve the solid in methanol
  5. customA solid resulted which
  6. customwas recrystallized from ethanol

출처 및 근거

ORD 기록
ord-509a55169a9d4f9bb06f44b0dee29643
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04743601

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