Phosgene → 5-Isocyanatoisoquinoline

HRID 2092177Notes

Reaction equation

HRID 2092177 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[CH:11]2>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N:5]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[CH:11]2)=[C:1]=[O:2]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 707665-Aminoisoquinoline

Product 1

HCID 115863575-Isocyanatoisoquinoline

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of phosgene (20% in toluene, 5.8 ml, 11 mmol) was added to 50 ml methylene chloride and cooled to 0° C. 4-Dimethylaminopyridine (2.86 g, 23.4 mmol) in 30 ml methylene chloride was added dropwise. A thick white suspension formed. A solution of 5-aminoisoquinoline (1.44 g, 10 mmol) in 30 ml methylene chloride was then added dropwise to this suspension. The reaction was allowed to warm to ambient temperature and stirred overnight. At the end of this time, a solution formed, and the solvent was removed under reduced pressure. The residue was triturated with 50 ml diethyl ether to give an approximately 0.1 M solution of 5-isocyanato-isoquinoline.

Workup

  1. customA thick white suspension formed
  2. temperatureto warm to ambient temperature
  3. customAt the end of this time, a solution formed
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was triturated with 50 ml diethyl ether

Sources & evidence

ORD record
ord-58a075dbd3a74f53beccdba8c0559d7b
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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