Pyridine → Phenyl isoquinolin-4-ylcarbamate

HRID 571989Notes

Reaction equation

HRID 571989 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH2:11])=[CH:3][N:2]=1.N1C=CC=CC=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>C(#N)C.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:11][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:3][N:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 902374-Aminoisoquinoline

Product 1

HCID 58442686Phenyl isoquinolin-4-ylcarbamateYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Isoquinolin-4-amine (296 mg, 2.05 mmol) was dissolved in acetonitrile. To the reaction mixture was added pyridine (0.20 mL, 2.46 mmol) and phenyl chloroformate (0.27 mL, 2.15 mmol), respectively and stirred at room temperature for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The crude was purified by column chromatography to give phenyl isoquinolin-4-ylcarbamate (318 mg, 59%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-115e81effb614df49d9fdd22c812890e
Source dataset
uspto-grants-2015_05
Patent number
US09029378B2

Reaction notes

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