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

HRID 2165845Notes

Reaction equation

HRID 2165845 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-185e18e3081d4004a94bbe8566882b10
Source dataset
uspto-grants-1990_07
Patent number
US04942168

Reaction notes

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