Potassium Hydroxide → 2-(2'-Fluoro-1,1'-Biphenyl-4-yl)-3-Methyl-6-(2-Aminoethyl)-4-Quinolinecarboxylic Acid

HRID 275498Notes

Reaction equation

HRID 275498 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[C:11]2=O)=O.[CH3:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:36]([F:37])=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)=O.[OH-:38].[K+]>C(O)C.O>[F:37][C:36]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:28]1[CH:29]=[CH:30][C:25]([C:23]2[C:22]([CH3:21])=[C:11]([C:12]([OH:17])=[O:38])[C:10]3[C:14](=[CH:15][CH:16]=[C:8]([CH2:7][CH2:6][NH2:5])[CH:9]=3)[N:13]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 27374901-(2'-Fluoro[1,1'-biphenyl]-4-yl)propan-1-oneHCID 197085645-(2-Trifluoroacetylaminoethyl)-isatin

Product 1

HCID 197085652-(2'-Fluoro-1,1'-Biphenyl-4-yl)-3-Methyl-6-(2-Aminoethyl)-4-Quinolinecarboxylic AcidYield 62.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

5-(2-trifluoroacetylaminoethyl)-isatin (572 mg, 2.0 mmol) and 4-(2-fluorophenyl)propiophenone (457 mg, 2.0 mmol) were suspended in ethanol (6 ml) and treated with a solution of KOH (1.01 g, 18.0 mmol) in water (3 ml). The mixture was heated at reflux for 48 hours. The mixture was then cooled, diluted with additional water, concentrated in vacuo to remove the ethanol, and filtered. The solid was washed with water, and the combined aqueous filtrate was adjusted to pH 8 with dilute aqueous HCl. The resulting solid was collected by filtration, rinsed thoroughly with water and dried to provide the title hapten as a cream-colored solid (500 mg, 62%): mp>250° C.; NMR (CF3COOD) δ 8.61 (d, 1H), 8.44 (s, 1H), 8.33 (d, 1H), 8.12 (d, 2H), 7.95 (d, 2H), 7.69 (t, 1H), 7.57 (m, 1H), 7.43 (t, 1H), 7.35 (m, 1H), 3.92 (bs, 2H), 3.71 (bt, 2H), 2.95 (s, 3H); mass spec (NH3 -CI) m/z 401 (100%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 hours
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated in vacuo
  5. customto remove the ethanol
  6. filtrationfiltered
  7. washThe solid was washed with water
  8. filtrationThe resulting solid was collected by filtration
  9. washrinsed thoroughly with water
  10. customdried

Sources & evidence

ORD record
ord-58979d662515410395f3e60cf4c5fac5
Source dataset
uspto-grants-1995_02
Patent number
US05393891

Reaction notes

Loading…