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

HRID 2165845ノート

反応式

HRID 2165845 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

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 melting point of 151°-154° C.

後処理

  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

出典と根拠

ORDレコード
ord-185e18e3081d4004a94bbe8566882b10
出典データセット
uspto-grants-1990_07
特許番号
US04942168

反応ノート

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