4-Chloroquinoline → 681828-34-2

HRID 1352504Notes

Reaction equation

HRID 1352504 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH:12]1([NH2:15])[CH2:14][CH2:13]1>[OH-].[Na+]>[CH:12]1([NH:15][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 691404-ChloroquinolineHCID 69828Cyclopropylamine

Product 1

HCID 22935736681828-34-2Yield 42.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-chloroquinoline (13.9 g) and cyclopropyl amine (9.7 g) was heated at 180° C. under stirring for 16 hours. After cooling, a solution of sodium hydroxide 1N (200 ml) was added. After extraction with dichloromethane (200 ml), the organic layer was separated and dried over sodium sulfate. The solvent was removed under reduce pressure to afford an oil, which was crystallized in acetonitrile (50 ml). Cyclopropyl-quinolin-4-yl-amine (6.6 g; 42% yield) was obtained after filtration.

Workup

  1. temperatureAfter cooling
  2. extractionAfter extraction with dichloromethane (200 ml)
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. customto afford an oil, which
  7. customwas crystallized in acetonitrile (50 ml)

Sources & evidence

ORD record
ord-101b4c391dc143f3a370737c41a1a6b8
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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