3-Aminoquinoline → HCID 13078459, compound

HRID 863301Notes

Reaction equation

HRID 863301 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][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]([NH: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 113753-AminoquinolineHCID 12228Methyl Isocyanate2×

Product 1

HCID 13078459HCID 13078459, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.99 ml of methyl isocyanate is added to a solution of 2.0 g of 3-aminoquinoline in 15 ml of methylene chloride under argon and the mixture is heated under reflux for 2 h. A further 0.95 ml of methyl isocyanate is added and the reaction mixture is refluxed again for 2 h. The crude product is chromatographed over 100 g of silica gel (mobile phase gradient from L to P). This gives the title compound as a crystalline solid: Rf (L)=0.2; M+=201.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 h
  3. temperaturethe reaction mixture is refluxed again for 2 h
  4. customThe crude product is chromatographed over 100 g of silica gel (mobile phase gradient from L to P)

Sources & evidence

ORD record
ord-aafb403a1c954167aa0621551d30a6cc
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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