Pyridine → Phenyl isoquinolin-1-ylcarbamate

HRID 571992Notes

Reaction equation

HRID 571992 reaction equation
[C:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[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>[C:1]1([NH:11][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 737421-Isoquinolinamine

Product 1

HCID 86676325Phenyl isoquinolin-1-ylcarbamateYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Isoquinolin-1-amine (300 mg, 2.08 mmol) was dissolved in acetonitrile. The reaction mixture was added pyridine (0.02 mL, 2.50 mmol) and phenyl chloroformate (0.27 mL, 2.18 mmol) 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-1-ylcarbamate (285 mg, 52%).

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-33a8d047ecd44e31990e8c3b57afeb97
Source dataset
uspto-grants-2015_05
Patent number
US09029378B2

Reaction notes

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