Ethanol → HCID 22936764, compound

HRID 387731Notes

Reaction equation

HRID 387731 reaction equation
O1CCCC1.C(O)C.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[O:23][C:24]1[CH:29]=[CH:28][C:27](=[N:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[N+:38]([O-:40])=[O:39])[CH2:26][CH:25]=1.[BH4-].[Na+]>O.C(Cl)(Cl)Cl>[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[O:23][C:24]1[CH:25]=[CH:26][C:27]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[N+:38]([O-:40])=[O:39])=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 67202966HCID 67202966, compound

Product 1

HCID 22936764HCID 22936764, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

After adding tetrahydrofuran (2 ml), ethanol (2 ml) and chloroform (1 ml) to 6,7-dimethoxy-4-(4-(2-nitrophenylmethyl-imino)phenyloxy)quinoline (200 mg, 0.4657 mmol) and heating the mixture to complete dissolution, sodium borohydride (35 mg, 0.9314 mmol) was added and the mixture was heated to reflux for 1 hour and 30 minutes. After cooling to room temperature, water was added, the mixture was extracted with ethyl acetate, washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with an NH silica gel column (hexane-ethyl acetate system) to obtain the title compound (151 mg, 0.3500 mmol, 75.15%) as a yellow oil.

Workup

  1. temperatureheating the mixture
  2. additionwas added
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 1 hour and 30 minutes
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified with an NH silica gel column (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-0d429ebf19c04b3298e2e467ef59a1a3
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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