3-Hydroxyquinoline → HCID 19697839, compound

HRID 863312Notes

Reaction equation

HRID 863312 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[OH:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2>C(Cl)Cl>[CH3:1][NH:2][C:3]([O:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:4]

Participants

4

Reactant 2

HCID 113763-HydroxyquinolineHCID 12228Methyl Isocyanate

Product 1

HCID 19697839HCID 19697839, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.98 ml of methyl isocyanate is added to a suspension of 1.0 g of 3-hydroxyquinoline in 8 ml of methylene chloride and the reaction mixture is heated under reflux for 5 h. Purification by chromatography over 50 g silica gel (mobile phase J) gives 3-(methylaminocarbonyloxy)quinoline as a solid: Rf (L)=0.26.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 5 h
  3. customPurification by chromatography over 50 g silica gel (mobile phase J)

Sources & evidence

ORD record
ord-e57fda3ec8e740f5855fde716232c8df
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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