Carbon Tetrachloride → (R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 418484Notes

Reaction equation

HRID 418484 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]([C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[CH3:17])[C:7]2=[O:12].C(Cl)(Cl)(Cl)[Cl:21].ClN1C(=O)CCC1=O.CN(C)C=O>ClCCl>[C:16]([O:15][CH2:14][C@H:13]([N:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:21])[C:2]=2[NH2:1])[C:7]1=[O:12])[CH3:19])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 59515825(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59515650(R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of acetic acid (R)-2-(5-amino-1-oxo-1H-isoquinolin-2-yl)-propyl ester (20 g, 0.07 mol) in carbon tetrachloride (400 mL, 4 mol) at 60° C. was added a solution of N-chlorosuccinimide (11 g, 0.082 mol) in N,N-dimethylformamide (140 mL, 1.8 mol) in 50 minutes. The mixture was stirred at 60° C. for an additional 15 minutes. The cooled mixture was diluted with dichloromethane (400 mL), washed with sodium bicarbonate (100 mL×3), and concentrated under reduced pressure. The mixture was purified by flash chromatography to afford the desired product as a brown oil.

Workup

  1. washwashed with sodium bicarbonate (100 mL×3)
  2. concentrationconcentrated under reduced pressure
  3. customThe mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-47a255b9aa99441088a94f693941d4d1
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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