Acetyl chloride → Ethyl(acetyloxy)(isoquinolin-5-yl)acetate

HRID 887198Notes

Reaction equation

HRID 887198 reaction equation
[OH:1][CH:2]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]=[CH:13]2)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:18](Cl)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:1][CH:2]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]=[CH:13]2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 11368232Ethyl Hydroxy(isoquinolin-5-yl)acetate

Product 1

HCID 86589025Ethyl(acetyloxy)(isoquinolin-5-yl)acetateYield 67.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product of Example 70B (1.0202 g, 4.41 mmol) in pyridine (15 mL) was treated with acetyl chloride (0.35 mL, 4.92 mmol) dropwise. The solution was stirred at room temperature for 4 hours and concentrated under reduced pressure. The residue was purified by column chromatography (2% methanol/CH2Cl2) to provide the title compound as yellow oil (0.8100 g, 67%). MS (ESI+) m/z 274 (M+H)+; 1H NMR (DMSO-d6, 300 MHz) δ 1.07 (t, J 7.1, 3H), 2.17 (s, 3H), 4.13 (m, 2H), 6.62 (s, 1H), 7.74 (m, 1H), 7.94 (d, J 7.1, 1H), 8.03 (d, J 6.1, 1H), 8.22 (d, J 7.6, 1H), 8.60 (d, J 5.7, 1H), 9.39 (s, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography (2% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-4f45bdcbdea14bdfbd8104388e70b5e1
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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