Aniline → N-phenylquinolin-4-amine

HRID 1352498Notes

Reaction equation

HRID 1352498 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.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[OH-].[Na+]>[C:13]1([NH:12][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 691404-Chloroquinoline

Product 1

HCID 5124249N-phenylquinolin-4-amineYield 101.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloroquinoline (10 g) and aniline (11.4 g) was warmed to 150° C. for 30 min. A solution of sodium hydroxide 1 N (200 ml) was added. After extraction with ethyl acetate (1 L), the organic layer was separated and dried over sodium sulfate. The solvent was removed to afford an amorphous materiel, which was crystallized in cyclohexane. Phenyl-quinolin-4-yl-amine (13.7 g) was obtained after filtration.

Workup

  1. extractionAfter extraction with ethyl acetate (1 L)
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed
  5. customto afford an amorphous materiel, which
  6. customwas crystallized in cyclohexane

Sources & evidence

ORD record
ord-bc16656bbf82477d8617d02915ddd810
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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