Hydrochloric Acid → HCID 178522923, compound

HRID 2289905Notes

Reaction equation

HRID 2289905 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](=[C:23]([F:26])[C:24]=1[F:25])[N:21]=[CH:20][C:19]([C:27](OCC)=[O:28])=[C:18]2[OH:32].Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:27]([C:19]2[CH:20]=[N:21][C:22]3[C:17]([C:18]=2[OH:32])=[CH:16][C:15]([F:14])=[C:24]([F:25])[C:23]=3[F:26])=[O:28])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 660364-ChlorobenzylamineHCID 27339723-Quinolinecarboxylic acid, 1,4-dihydro-4-oxo-6,7,8-trifluoro-, ethyl esterHCID 16682925Trimethylaluminum

Product 1

HCID 178522923HCID 178522923, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-chlorobenzylamine (0.45 mL) in 5 mL of toluene is added 1.84 mL of a 2.0 M solution of trimethylaluminum in toluene. The solution is stirred for 5 min at 0° C. and then 0.20 g of ethyl 6,7,8-trifluoro-4-hydroxy-3-quinolinecarboxylate (Tetrahedron 48, 29 (1992)) is added. The solution is stirred at 0° C. for an additional 30 min and then it is stirred 18 h at 25° C. The mixture is poured onto a mixture of 50 mL of 3 M hydrochloric acid and 50 mL of crushed ice. The mixture is extracted with three successive 75 mL portions of ethyl acetate. The combined extracts are dried (MgSO4) and the solvent is evaporated at reduced pressure. The residue is dissolved in a small volume of ethyl acetate and hexanes is added until the solution becomes cloudy. The mixture is then allowed to stand for 1 h. Filtration of this mixture gives the desired amide as 0.25 g of a solid.

Workup

  1. stirringThe solution is stirred at 0° C. for an additional 30 min
  2. stirringit is stirred 18 h at 25° C
  3. extractionThe mixture is extracted with three successive 75 mL portions of ethyl acetate
  4. dry with materialThe combined extracts are dried (MgSO4)
  5. customthe solvent is evaporated at reduced pressure
  6. dissolutionThe residue is dissolved in a small volume of ethyl acetate and hexanes
  7. additionis added until the solution
  8. waitto stand for 1 h
  9. filtrationFiltration of this mixture

Sources & evidence

ORD record
ord-078eb0320e784100b3c87e6cfdc51750
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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