Hydrochloric Acid → HCID 178522875, compound

HRID 2289900Notes

Reaction equation

HRID 2289900 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C[Al](C)C.[F:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][C:19]([C:25](OCC)=[O:26])=[C:18]2[OH:30].Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:25]([C:19]2[CH:20]=[N:21][C:22]3[C:17]([C:18]=2[OH:30])=[CH:16][C:15]([F:14])=[CH:24][CH:23]=3)=[O:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 660364-ChlorobenzylamineHCID 16682925TrimethylaluminumHCID 178469553HCID 178469553, compound

Product 1

HCID 178522875HCID 178522875, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-chlorobenzylamine (0.52 mL) in 5 mL of toluene is added 2.13 mL of a 2.0 M solution of trimethylaluminum in tolune. The solution is stirred for 5 min at 0° C. and then a suspension of 0.50 g of ethyl 6-fluoro-4-hydroxy-3-quinolinecarboxylate (J. Amer. Chem. Soc., 69, 371 (1947)) in 5 mL of toluene is added. The solution is stirred at 0° C. for an additional 10 min and then it is stirred 18 h at 90° C. The mixture is cooled to 25° C. and it is poured onto a mixture of a large excess of 3 M hydrochloric acid and ice. After stirring the mixture vigorously for 30 min it is filtered. The solid is dissolved in 50 mL of warm glacial acetic acid and distilled water is added to the resulting solution until it is cloudy. The mixture is then allowed to stand for several hours at 5° C. Filtration of this mixture gives the desired amide as 390 mg of a solid.

Workup

  1. additionis added
  2. stirringThe solution is stirred at 0° C. for an additional 10 min
  3. stirringit is stirred 18 h at 90° C
  4. temperatureThe mixture is cooled to 25° C.
  5. stirringAfter stirring the mixture vigorously for 30 min it
  6. filtrationis filtered
  7. dissolutionThe solid is dissolved in 50 mL of warm glacial acetic acid
  8. distillationdistilled water
  9. additionis added to the resulting solution until it
  10. waitto stand for several hours at 5° C
  11. filtrationFiltration of this mixture

Sources & evidence

ORD record
ord-84ae2a98a54441bf8f94912230f413df
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…