Phosgene → 5-Isocyanato-3-methylisoquinoline

HRID 2092166Notes

Reaction equation

HRID 2092166 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][C:6]1[N:7]=[CH:8][C:9]2[C:14]([CH:15]=1)=[C:13]([NH2:16])[CH:12]=[CH:11][CH:10]=2>CN(C)C1C=CN=CC=1.ClCCl.O1CCCC1>[CH3:5][C:6]1[N:7]=[CH:8][C:9]2[C:14]([CH:15]=1)=[C:13]([N:16]=[C:1]=[O:2])[CH:12]=[CH:11][CH:10]=2

Participants

6

Reactant 2

HCID 6371PhosgeneHCID 122120553-Methylisoquinolin-5-amine

Product 1

HCID 222283825-Isocyanato-3-methylisoquinoline

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phosgene (20% in toluene, 2.9 mL, 5.5 mmol) of dichloromethane (30 mL) was cooled to 0° C. and treated dropwise with a solution of 4-dimethylaminopyridine (1.43 g, 11.7 mL) in dichloromethane (15 mL). A thick white suspension formed. A solution of 3-methyl-isoquinolin-5-ylamine (0.79 g, 5 mmol) in tetrahydrofuran (20 mL) was then added dropwise to this suspension. The reaction mixture was allowed to warm to ambient temperature and stirred overnight, the solvent was removed under reduced pressure, and the residue titurated with 50 mL of diethyl ether to give an approximately 0.1 M solution of 3-methyl-5-isocyanato-isoquinoline.

Workup

  1. customA thick white suspension formed
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fca9c962776348f8bd31c9fe1fb14036
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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