Ethyl Acetate → 5-nitroquinoline-2-carbaldehyde

HRID 2182696Notes

Reaction equation

HRID 2182696 reaction equation
I([O-])(=O)(=O)=O.[Na+].OC([N:11]1[C:20]2[C:15](=[C:16]([N+:21]([O-:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH2:12]1)CO.[C:24](OCC)(=[O:26])C>O1CCCC1.O>[N+:21]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[CH:14]=[CH:13][C:12]([CH:24]=[O:26])=[N:11]2)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21948859HCID 21948859, compoundHCID 23667635Sodium periodate

Product 1

HCID 47370745-nitroquinoline-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.99 g (14.0 mmol) of sodium periodate is added to a solution that consists of 1.64 g (7.0 mmol) of 1-(1,2-dihydroxyethyl)-5-nitroquinoline in 42 ml of tetrahydrofuran and 7.0 ml of water. After 20 hours at room temperature, ethyl acetate is added, and the organic phase is washed with saturated sodium chloride solution. After the organic phase is dried on sodium sulfate, after the solvent is removed, and after purification on silica gel with hexane-ethyl acetate (0-100%), 1.40 g (99% of theory) of the product is obtained.

Workup

  1. washthe organic phase is washed with saturated sodium chloride solution
  2. customAfter the organic phase is dried on sodium sulfate
  3. customafter the solvent is removed
  4. customafter purification on silica gel with hexane-ethyl acetate (0-100%), 1.40 g (99% of theory) of the product
  5. customis obtained

Sources & evidence

ORD record
ord-43140309c1a54f0b9d4d6d7a27a95f5f
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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