Ethyl Acetate → Quinoline-4-carbaldehyde 1-oxide

HRID 2112799Notes

Reaction equation

HRID 2112799 reaction equation
[O-:1][N+:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][OH:13])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+].C(OCC)(=O)C>C(#N)C>[N+:2]1([O-:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 21963888(1-Oxidoquinolin-4-yl)methanol

Product 1

HCID 11229066Quinoline-4-carbaldehyde 1-oxide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a vigorously stirring suspension of (1-oxidoquinolin-4-yl)methanol (0.10 g, 0.57 mmol) in acetonitrile (10 mL) was added Dess-Martin periodinane (0.47 g, 0.63 mmol). After 1 h, 2M NaOH (aq, 2 mL) and ethyl acetate (105 mL) were added and the reaction was stirred for 5 min. The layers were then separated and the organic phase was washed with saturated NaHCO3 (aq), brine, and dried over MgSO4, filtered, and concentrated in vacuo to a light yellow solid. MS (ES+): 174 [MH+].

Workup

  1. stirringthe reaction was stirred for 5 min
  2. customThe layers were then separated
  3. washthe organic phase was washed with saturated NaHCO3 (aq), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a light yellow solid

Sources & evidence

ORD record
ord-28d9fda4a9984fcab2b18ce9491b38b7
Source dataset
uspto-grants-2009_04
Patent number
US07524859B2

Reaction notes

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