Methyl 2-nitroacetate → HCID 20136729, compound

HRID 1593646Notes

Reaction equation

HRID 1593646 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.Cl.C(NCC)C.[N+:17]([CH2:20][C:21](OC)=[O:22])([O-:19])=[O:18]>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:9]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:10][C:21](=[O:22])[C:20]([N+:17]([O-:19])=[O:18])=[CH:7]2

Participants

6

Reactant 3

HCID 17206Methyl 2-nitroacetateHCID 27373285-FluorosalicylaldehydeHCID 10197650Diethylammonium chloride

Product 1

HCID 20136729HCID 20136729, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

5-Fluoro-2-hydroxybenzaldehyde (7.14 g, 50.96 mmol), diethyl amine hydrochloride (6.70 g, 61.15 mmol) and methyl nitroacetate (5.62 mL, 61.15 mmol) were added together in toluene (90 mL) and stirred together at reflux under a N2 atmosphere. A Dean-Stark apparatus was fitted to the system to remove the H2O generated by the reaction. The reaction was allowed to reflux overnight, after which the mixture was cooled and diluted with H2O. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4 and concentrated. Purification by flash chromatography on silica gel afforded the product as an orange solid (5.90 g, 55%)

Workup

  1. temperatureat reflux under a N2 atmosphere
  2. customA Dean-Stark apparatus was fitted to the system
  3. customto remove the H2O
  4. customgenerated by the reaction
  5. temperatureto reflux overnight
  6. temperatureafter which the mixture was cooled
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated
  11. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-349d40d6085e4a77b02d808096f54c94
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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