Ethyl(acetyloxy)(isoquinolin-5-yl)acetate → Ethyl 2-(isoquinolin-5-yl)acetate

HRID 887199Notes

Reaction equation

C(O[CH:5]([C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][N:15]=[CH:16]2)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)C>C(O)C>[CH:16]1[C:17]2[C:12](=[C:11]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:14][N:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The product of Example 70C (1.43 g, 5.23 mmol) in absolute ethanol (200 mL) was treated with dry 10% Pd/C (0.122 g) and triethylamine (10.4 mL). The reaction mixture was stirred at 60° C. for 6 hours under H2 (60 psi), filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography (5% methanol/CH2Cl2) to provide the title compound as light brown oil (0.93 g, 67%). MS (ESI+) m/z 216 (M+H)+, (ESI−) m/z 214 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 1.17 (t, J 7.1, 3H), 4.09 (q, J 7.1, 2H), 4.17 (s, 2H), 7.64 (m, 1H), 7.72 (d, J 6.2, 1H), 7.81 (d, J 5.7, 1H), 8.07 (d, J 7.9, 1H), 8.54 (d, J 6.1, 1H), 9.33 (s, 1H).

Workup

dry with materialwith dry 10% Pd/C (0.122 g) and triethylamine (10.4 mL)
filtrationfiltered
concentrationthe filtrate concentrated under reduced pressure
customThe residue was purified by column chromatography (5% methanol/CH2Cl2)

Sources & evidence

ORD record: ord-3dab98c2cb874eee997516c253e460ec
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247413B2

Reaction notes

Loading…