Hydrochloric Acid → HCID 178522924, compound

HRID 2289904Notes

Reaction equation

HRID 2289904 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[C:24]([F:25])=[C:23]([F:26])[C:22]([F:27])=[C:21]2[C:16]=1[C:17]([OH:33])=[C:18]([C:28](OCC)=[O:29])[CH:19]=[N:20]2.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:28]([C:18]2[CH:19]=[N:20][C:21]3[C:16]([C:17]=2[OH:33])=[C:15]([F:14])[C:24]([F:25])=[C:23]([F:26])[C:22]=3[F:27])=[O:29])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 660364-ChlorobenzylamineHCID 16682925TrimethylaluminumHCID 178469652HCID 178469652, compound

Product 1

HCID 178522924HCID 178522924, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-chlorobenzylamine (0.080 mL) in 5 mL of toluene is added 0.70 mL of a 2.0 M solution of trimethylaluminum in toluene. The solution is stirred for 5 min at 0° C. and then a suspension of 0.20 g of ethyl 5,6,7,8-tetrafluoro-4-hydroxy-3-quinolinecarboxylate (U.S. Pat. No. 4,940,710) in 5 mL of toluene is added. The solution is stirred at 0° C. for an additional 10 min and then it is stirred 3 h at 90° C. The mixture is cooled to 25° C. and it is poured onto a mixture of 10 mL of 3 M hydrochloric acid and 10 mL of crushed ice. After stirring the mixture vigorously for 20 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 h at 5° C. Filtration of this mixture gives the desired amide as 0.12 g of a solid.

Workup

  1. stirringThe solution is stirred at 0° C. for an additional 10 min
  2. stirringit is stirred 3 h at 90° C
  3. temperatureThe mixture is cooled to 25° C.
  4. stirringAfter stirring the mixture vigorously for 20 min it
  5. filtrationis filtered
  6. dissolutionThe solid is dissolved in 50 mL of warm glacial acetic acid
  7. distillationdistilled water
  8. additionis added to the resulting solution until it
  9. customto stand for several h at 5° C
  10. filtrationFiltration of this mixture

Sources & evidence

ORD record
ord-46ae08910d0a407db7628e65092c8515
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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