Cyclohexylamine → HCID 22417951, compound

HRID 1720275Notes

Reaction equation

HRID 1720275 reaction equation
[BrH:1].Cl[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>>[OH2:13].[BrH:1].[CH:14]1([NH:20][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=3)[N:6]=[CH:5][CH:4]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 22417838HCID 22417838, compound

Product 1

HCID 22417951HCID 22417951, compoundYield 40%

Procedure

A solution of 245 mg (0.94 mmol) of 4-chloroquinolin-6-ol hydrobromide and 1.0 mL of cyclohexylamine was heated under reflux overnight. Excess volatile components of the reaction mixture were evaporated under reduced pressure. The residue was slurried with isopropyl ether and then filtered. The solids were recrystallized from hot acetic acid to afford 129 mg (40%) of the title compound: m.p. 280°-285° C. (dec.).

Workup

  1. temperatureunder reflux overnight
  2. customExcess volatile components of the reaction mixture were evaporated under reduced pressure
  3. filtrationfiltered
  4. customThe solids were recrystallized from hot acetic acid

Sources & evidence

ORD record
ord-e239a5ba98ae46e59c515ed191179ee0
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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