Ethyl Acetate → 5-nitroquinoline-2-carbaldehyde

HRID 2054976Notes

Reaction equation

HRID 2054976 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-b79ca8c747c042d0b04597976a8a969f
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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