Ethyl Acetate → HCID 86631140, compound

HRID 912706Notes

Reaction equation

HRID 912706 reaction equation
O[C:2]1([CH:8]=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1.I[CH2:11][CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-:16].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH2:11]([O:16][C:7]1[C:2]([CH:8]=[O:9])=[N:3][CH:4]=[CH:5][CH:6]=1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 86631141HCID 86631141, compound

Product 1

HCID 86631140HCID 86631140, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was made in a related procedure described by Daines, R. A. et al. (J. Med. Chem. 1993, 36, 3321-3332). To a solution of 2-hydroxy-pyridine-2-carbaldehyde (0.998 g, 8.11 mmol) in DMF (11.4 mL) was added 1-iodobutane (1.10 mL, 9.73 mmol) followed by anhydrous potassium carbonate (3.36 g, 24.3 mmol). After 1 h at 90° C., the solution was cooled to r.t. and poured into ethyl acetate. The organic layer was washed once with water, twice with brine and then was dried over sodium sulfate, filtered and concentrated in vacuo generating 1.31 g (90% yield, 7.30 mmol) of the title compound as a liquid. This material was used in the next step without further purification.

Workup

  1. washThe organic layer was washed once with water, twice with brine
  2. dry with materialwas dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f48ce56d5a88438f922b6eadab4ad3e5
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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