Ethyl 2-(isoquinolin-5-yl)acetate → 2-(Isoquinolin-5-YL)acetic acid

HRID 586015Notes

Reaction equation

HRID 586015 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([CH2:11][C:12]([O:14]CC)=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[OH-].[Na+].O>OS(O)(=O)=O>[CH:1]1[C:10]2[C:5](=[C:6]([CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 22032613Ethyl 2-(isoquinolin-5-yl)acetateHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 120187082-(Isoquinolin-5-YL)acetic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 5-isoquinolinylacetate (1.15 g, 5.34 mmol) was dissolved in concentrated H2SO4 (12 mL) and heated at 100° C. for 2 hours. The reaction mixture was poured into ice (20 g) and the pH was adjusted to 6 with 50% NaOH/H2O. The mixture was allowed to set of several hours, filtered, and the filter cake was rinsed with water to provide the title compound. MS (ESI+) m/z 188 (M+H)+; 1H NMR (DMSO, 300 MHz) δ 4.07 (s, 2H), 7.67 (m, 2H), 7.83 (d, J 5.7, 1H), 8.05 (d, J 8.1, 1H), 8.53 (d, J 6.1, 1H), 9.32 (s, 1H), 12.50 (s, 1H); 13C NMR (DMSO, 75 MHz) δ 37.6 (CH2CO), 117.1 (CH, C4), 126.8, 127.0 (CH, C7 & C8), 128.4 (C), 131.1 (C), 132.0 (CH, C6), 134.4 (C), 143.0 (CH, C3), 152.7 (CH, C1), 172.3 (CO); Anal. Calcd for C11H9NO2: C, 70.58; H, 4.85; N, 7.48. Found: C, 70.42; H, 4.93; N, 7.34.

Workup

  1. waitto set of several hours
  2. filtrationfiltered
  3. washthe filter cake was rinsed with water

Sources & evidence

ORD record
ord-b5a8aea49a384364a242346b20258b8e
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

Loading…