Diethylethanolamine → 2-Diethylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

HRID 326652Notes

Reaction equation

HRID 326652 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=2[Cl:19])[N:12]=[C:11]([C:21]([OH:23])=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:28]([N:30]([CH2:34][CH3:35])[CH2:31][CH2:32]O)[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=2[Cl:19])[N:12]=[C:11]([C:21]([O:23][CH2:29][CH2:28][N:30]([CH2:34][CH3:35])[CH2:31][CH3:32])=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7497DiethylethanolamineHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 214789594-Benzyloxy-5,7-dichloroquinoline-2-carboxylic acid

Product 1

HCID 197351892-Diethylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-benzyloxy-5,7-dichloroquinoline-2-carboxylic acid (1.7 g), was added thionyl chloride (10 ml) and the mixture was heated to reflux for 2 hours. The mixture was cooled to room temperature, excess thionyl chloride removed under reduced pressure to give an off white solid, to which was added dry tetrahydrofuran (20 ml). The solution was cooled to 0° C. and N,N-diethylethanolamine (2.1 ml) added dropwise. The reaction was left to warm to room temperature over 1 hour, poured into 10% sodium carbonate (100 ml) and extracted with ethyl acetate (3×100 ml). The organic layers were combined and washed with water (2×100 ml), brine (2×50 ml) and dried over magnesium sulphate. The solvent was removed under reduced pressure and the crude product purified by column chromatography to give 2-diethylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (1.1 g). δ (360 MHz, DMSO-d6), 0.99 (1H, t, CH2CH3), 2.54 (4H, q, CH2CH3), 2.81 (2H, t, CH2N), 4.41 (2H, m, CO2CH2), 5.50 (2H, s, OCH2), 7.41 (3H, m, o,p-ArH). 7.60 (2H, d, m-ArH), 7.71 (1H, s, 3-H), 7.86 (1H, d, 6-H) and 8.12 (1H, d, 8-H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customexcess thionyl chloride removed under reduced pressure
  4. customto give an off white solid
  5. temperatureThe solution was cooled to 0° C.
  6. waitThe reaction was left
  7. temperatureto warm to room temperature over 1 hour
  8. extractionextracted with ethyl acetate (3×100 ml)
  9. washwashed with water (2×100 ml), brine (2×50 ml)
  10. dry with materialdried over magnesium sulphate
  11. customThe solvent was removed under reduced pressure
  12. customthe crude product purified by column chromatography

Sources & evidence

ORD record
ord-f35c51dcfa57440ca02cd5e7ca4d0e34
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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