HCID 86680402, compound → HCID 86680401, compound

HRID 1023159Notes

Reaction equation

HRID 1023159 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>CO.[Pt](=O)=O>[NH:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86680402HCID 86680402, compound

Product 1

HCID 86680401HCID 86680401, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(quinolin-6-yloxy)acetate (0.3 g, 1.297 mmol) in MeOH (70 mL) was added Platinum(IV) oxide (0.08 g, 0.352 mmol) under N2 atmosphere. The reaction was stirred under 3 kg H2 pressure at RT for 18 hrs. The reaction was filtered through Celite, washed with methanol, and the filtrate was concentrated to afford ethyl 2-((1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetate as a yellow gum (0.25 g 85%). 1H NMR: 400 MHz, DMSO-d6: δ 1.20 (t, J=7.20 Hz, 3H), 1.76 (t, J=6.40 Hz, 2H), 2.62 (t, J=6.00 Hz, 2H), 3.11 (dd, J=2.00, 7.20 Hz, 2H), 4.13 (q, J=7.20 Hz, 2H), 4.56 (s, 2H), 5.26 (s, 1H), 6.35 (d, J=8.40 Hz, 1H), 6.47-6.51 (m, 2H), 6.58-6.61 (m, 1H).

Workup

  1. filtrationThe reaction was filtered through Celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-69df454ab91546e398fa9ed8569ad280
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

Loading…