Sodium hydride → HCID 18353762, compound

HRID 430068Notes

Reaction equation

HRID 430068 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][OH:10].[H-].[Na+].Cl[C:18]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1>C1COCC1>[NH3:6].[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][O:10][C:18]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 4183093-{[(3,4-Dichlorophenyl)methyl]amino}propan-1-olHCID 183536712-Chloro-4-(4-methoxybenzyloxy)quinoline

Product 2

HCID 222AmmoniaHCID 18353762HCID 18353762, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(3,4-dichlorobenzylamino)propanol (47 mg, 0.2 mmol) in dry THF (0.5 ml) was added to a suspension of sodium hydride (60% dispersion in oil, 8.0 mg, 0.2 mmol) at room temperature under an argon atmosphere. After 10 min the mixture was heater to reflux for a further 20 min. A solution of 2-chloro-4-(4-methoxybenzyloxy)quinoline (62 mg, 0.2 mmol) in dry THF (0.5 ml) was added and reflux continued under an argon atmosphere for a further 30 min. The solvent was evaporated, the residue dissolved in toluene and applied to a column of Kieselgel 60. Elution with a mixture of 70:29:1 ethyl acetate:hexane:2M methanolic ammonia afforded the title compound as a colourless oil (17 mg, 17%); δH (CDCl3) 1.6 (1H, br. s.), 1.97-2.12 (2H, m), 2.79 (2H, t, J=6.8 Hz), 3.76 (2H, s), 3.84 (3H, s), 4.57 (2H, t, J=6.2 Hz), 5.14 (2H, s), 6.27 (2H, s), 6.96 (2H, d, J=8.6 Hz), 7.13-7.44 (6H, m), 7.58 (1H, dt, J=1.1, 7.1 Hz), 7.70 (1H, d, J=8.2 Hz), 8.09 (1H, d, J=8.2 Hz); MS (ES+) 497 (MH+, 50%), 216 (100).

Workup

  1. temperatureheater to reflux for a further 20 min
  2. temperaturereflux
  3. waitcontinued under an argon atmosphere for a further 30 min
  4. customThe solvent was evaporated
  5. dissolutionthe residue dissolved in toluene
  6. washElution
  7. additionwith a mixture of 70:29:1 ethyl acetate

Sources & evidence

ORD record
ord-5f9c6cf5a5b640798e8743f9621d785b
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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