Sodium Iodide → HCID 4737192, compound

HRID 1274980Notes

Reaction equation

HRID 1274980 reaction equation
[N+:1]([C:4]1[CH:11]=[C:8]([CH:9]=[O:10])[C:7]([OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C1COCC1>[CH2:18]([O:17][C:15]([CH2:14][O:12][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]=1[CH:9]=[O:10])=[O:16])[CH3:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 668085-Nitrosalicylaldehyde

Product 1

HCID 4737192HCID 4737192, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-nitrosalicylaldehyde (Aldrich) (0.167 g, 1.0 mmol), ethyl bromoacetate (0.166 g, 1.0 mmol), K2CO3 (0.276 g, 2.0 mmol) and NaI (0.015 g, 0.1 mmol) in THF (10 mL) is heated to 80° C. for 24 h. The solution is concentrated and the residue is purified by chromatography (silica gel, gradient, 5-20% CH3OH in CH2Cl2) to afford the title compound (0.20 g, 87%).

Workup

  1. concentrationThe solution is concentrated
  2. customthe residue is purified by chromatography (silica gel, gradient, 5-20% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-911bfcce870b44f1aea1312497e749ff
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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