Potassium Carbonate → Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetate

HRID 1492304Notes

Reaction equation

HRID 1492304 reaction equation
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=O)N2)C.Br[CH2:17][C:18]1[CH:36]=[CH:35][C:21]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:20][CH:19]=1.C(=O)([O-])[O-:38].[K+].[K+]>COCCOC>[CH2:13]([C:11]1[CH:10]=[C:9]([O:38][CH2:17][C:18]2[CH:36]=[CH:35][C:21]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:20][CH:19]=2)[C:4]2[CH2:5][CH2:6][CH2:7][CH2:1][C:3]=2[N:12]=1)[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18952399Ethyl 2-(4-bromomethylphenoxy)phenylacetateHCID 200942525,7-diethyl-[1,6]naphthyridin-2(1H)-one

Product 1

HCID 18952389Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetateYield 43.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of compound H (404 mg), ethyl 2-(4-bromomethylphenoxy)phenylacetate (700 mg) and potassium carbonate (552 mg) in 1,2-dimethoxyethane (10 ml) was heated under reflux for 1 hour. Insoluble material was removed by filtration and the filtrate was concentrated. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (7:3 v/v), to give ethyl 2-[4-((5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl)phenoxy]phenylacetate (A) (390 mg), as a gum; NMR (CDCl3): 1.2(t, 3H), 1.25(t, 3H), 1.35(t, 3H), 2.8(q, 2H), 3.1(q, 2H), 4.1-4.25(m, 2H), 5.4(s, 2H), 5.55(s, 1H), 6.7(d, 1H), 6.85(s, 1H), 6.9(d, 2H), 7.15(d, 2H), 7.3-7.4(m, 3H), 7.5-7.6(m, 2H), 7.95(d, 1H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customInsoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (7:3 v/v)

Sources & evidence

ORD record
ord-a3b99e2d88b44529b5c8f6893c8e683d
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Reaction notes

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