Diethyl Ether → HCID 54122524, compound

HRID 1938348Notes

Reaction equation

HRID 1938348 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH2:15][C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[C:21]([C:26](OC)=[O:27])[CH:22]=[N:23]2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCOCC.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:27][CH2:26][C:21]1[CH:22]=[N:23][C:24]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([CH2:15][N:8]([CH3:7])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH:25]=2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2×HCID 54264545HCID 54264545, compound

Product 1

HCID 54122524HCID 54122524, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen atmosphere, lithium aluminum hydride (33 mg, 0.88 mmol.) was suspended in tetrahydrofuran (THF, 1 mL). Under chilling with ice, to this was dropwise added the above methyl 7-(methylphenylamino)methyl-quinoline-3-carboxylate (171 mg, 0.56 mmol.) in dry THF (1.5 mL). The resulting mixture was stirred under chilling with ice for 3 hours. To this were added ether (5 mL) and saturated aqueous sodium sulfate solution (3 mL), so that excessive lithium aluminum hydride was decomposed. The organic portion was recovered by decantation, and the residue was washed with ether. The ether washings were combined with the above recovered organic portion. The solvent was distilled off under reduced pressure to give the desired compound as a brown amorphous product (128 mg, yield: 82%).

Workup

  1. temperatureUnder chilling with ice
  2. temperatureunder chilling with ice for 3 hours
  3. customThe organic portion was recovered by decantation
  4. washthe residue was washed with ether
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-316d807dc2df4fc1b93168540907fb8c
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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