Dimethylformamide → HCID 13079887, compound

HRID 326041Notes

Reaction equation

HRID 326041 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.Br[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:18][CH:17]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 13472700HCID 13472700, compound

Product 1

HCID 13079887HCID 13079887, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4-hydroxyphenoxy)quinoline (2.4 g), ethyl 2-bromopropionate (2.1 g), anhydrous potassium carbonate (3.3 g) and dimethylformamide (50 ml) was stirred and heated at 80° C. for 4 hours. The mixture was poured into water (500 ml) and extracted with diethyl ether (2×100 ml). The ether extracts were dried, evaporated to dryness and then chromatographed on silica gel (100 g) with dichloromethane elution. Ethyl 2-[4-(3-quinolinyloxy)phenoxy]-propionate was obtained as a pale yellow oil (1.9 g). Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 8.75 (1H, d); 8.1 (1H, bd); 7.7-7.3 (4H, m); 7.0 (4H, s, phenoxy protons); 4.75 (1H, q, CH--CH3); 4.25 (2H, q, OCH2 --CH3); 1.65 (3H, d, CH--CH3); 1.25 (3H, t, OCH2 --CH3).

Workup

  1. extractionextracted with diethyl ether (2×100 ml)
  2. dry with materialThe ether extracts were dried
  3. customevaporated to dryness
  4. customchromatographed on silica gel (100 g) with dichloromethane elution

Sources & evidence

ORD record
ord-af1f9475f3a540e8a4a673aeaa258700
Source dataset
uspto-grants-1984_04
Patent number
US04444584

Reaction notes

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