Phosgene → 5-Isocyanatoisoquinoline

HRID 2092153Notes

Reaction equation

HRID 2092153 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>ClCCl.CN(C)C1C=CN=CC=1>[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×

Procedure

A solution of phosgene (20% in toluene, 2.9 mL, 5.5 mmol) in dichloromethane (30 mL) at 0° C. was treated with dropwise addition of 4-dimethylaminopyridine (1.43 g, 11.7 ml) in dichloromethane (15 mL). A thick white suspension formed. A solution of 5-aminoisoquinoline in 15 mL of dichloromethane was then added dropwise to this suspension. The reaction mixture 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 titurated with 50 mL of diethyl ether to give an approximately 0.1 M solution of 5-isocyanato-isoquinoline.

Workup

  1. customA thick white suspension formed
  2. customAt the end of this time, a solution formed
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5be9b28c50344a80a8f72c6445f8c15f
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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