Ethyl Acetate → HCID 4433850, compound

HRID 2376808Notes

Reaction equation

HRID 2376808 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C[CH2:11][O:12]C(C)=O>C(OCC)=O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][CH:11]=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 673264-Fluorobenzylamine

Product 1

HCID 4433850HCID 4433850, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8025Ethyl formateSolvent

Procedure

A solution of 4-fluorobenzylamine (20 g, 160 mmol) in ethyl formate was heated at reflux for 4 h. After cooling, the solvent was evaporated to afford a yellow solid. Trituration with cold EtOAc afforded the title compound as a white solid (17.46 g, 71%). 1H NMR (CDCl3): □ 8.24 (s, 1H), 7.25 (m, 2H), 7.00 (m, 2H), 5.91 (br s, 1H), 4.42 (d, 2H).

Workup

  1. temperatureat reflux for 4 h
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. customto afford a yellow solid

Sources & evidence

ORD record
ord-c56f9f6898c2443db4faf526a04be1dc
Source dataset
uspto-grants-2008_12
Patent number
US07468378B2

Reaction notes

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