Pyridine → Phenyl isoquinolin-5-ylcarbamate

HRID 12407

Reaction equation

HRID 12407 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14].N1C=CC=CC=1.O1CCCC1>ClCCl>[CH:7]1[C:8]2[C:3](=[C:2]([NH:1][C:13](=[O:14])[O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 15891Phenyl chloroformateHCID 707665-Aminoisoquinoline

Product 1

HCID 11380046Phenyl isoquinolin-5-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-aminoisoquinoline (2.7 g) were added phenyl chloroformate (2.85 ml), pyridine (2.0 ml) and tetrahydrofuran (50 ml), and the mixture was stirred for 3 hrs. The reaction mixture was diluted with dichloromethane, and washed with water and saturated aqueous sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. Diethyl ether was added to the residue, and the precipitate was collected by filtration to give the title compound (3 g).

Workup

  1. washwashed with water and saturated aqueous sodium hydrogen carbonate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated
  4. additionDiethyl ether was added to the residue
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-aba74c00bab547b9bde785f9f9547b37
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Linked notes

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