Potassium Carbonate → HCID 54381806, compound

HRID 845706Notes

Reaction equation

HRID 845706 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.[C:20]([N:22]([CH2:28][CH3:29])[C:23](=[O:27])[CH:24](Br)[CH3:25])#[N:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:20]([N:22]([CH2:28][CH3:29])[C:23](=[O:27])[CH:24]([O:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:7]2[CH:6]=[N:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=3)[N:8]=2)=[CH:14][CH:15]=1)[CH3:25])#[N:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133285004-[(6-Fluoro-2-quinoxalinyl)oxy]phenolHCID 53784648HCID 53784648, compound

Product 1

HCID 54381806HCID 54381806, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10 g (0.039 mole) of 4-(6-fluoroquinoxalin-2-yloxy)phenol, 9.6 g (0.047 mole) of 2-bromopropionic acid N-cyano-N-ethylamide and 8.1 g (0.058 mole) of potassium carbonate are stirred for 14 hours at room temperature in 100 ml of acetonitrile. The precipitated salts are removed by filtration and the filtrate is concentrated by evaporation. The residue is chromatographed through silica gel eluted with ethyl acetate/hexane (1:3), affording 7.1 g (48% of theory) of 2-[4-(6-fluoroquinoxalin-2-yloxy)phenoxy]propionic acid N-cyano-N-ethylamide with a melting point of 108°-111° C.

Workup

  1. customThe precipitated salts are removed by filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. customThe residue is chromatographed through silica gel
  4. washeluted with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-66bad6d235c74b9297051c90072fcf69
Source dataset
uspto-grants-1988_07
Patent number
US04759796

Reaction notes

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