Potassium Carbonate → HCID 54381806, compound

HRID 235561Notes

Reaction equation

HRID 235561 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-edf3c8ef417f4706b64022ee26e87aa1
Source dataset
uspto-grants-1987_02
Patent number
US04640703

Reaction notes

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