Triethylamine → HCID 19607855, compound

HRID 745073Notes

Reaction equation

HRID 745073 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)[CH2:7][CH2:6][CH2:5]2.C(N(CC)CC)C.[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([Cl:38])[CH:37]=1)[C:32](Cl)=[O:33]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:32](=[O:33])[C:31]3[CH:30]=[C:29]([Cl:28])[CH:37]=[C:36]([Cl:38])[CH:35]=3)=[CH:15][CH:14]=1)[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 761913,5-Dichlorobenzoyl chloride2×HCID 19607823HCID 19607823, compound

Product 1

HCID 19607855HCID 19607855, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Fluoro-1-(4-aminobenzoyl)-1,2,3,4-tetrahydroquinoline (0.15 g) is dissolved in dichloromethane (10 ml) and thereto is added triethylamine (0.31 ml). To the mixture is added dropwise a solution of 3,5-dichlorobenzoyl chloride (0.14 g) in dichloromethane (2.0 ml) under ice-cooling, and the mixture is stirred for 30 minutes under ice-cooling, and further, at room temperature for 1 hour. To the mixture are added triethylamine (0.31 ml) and 3,5-dichlorobenzoyl chloride (0.14 ml). The mixture is stirred at room temperature for 4 hours. The reaction mixture is washed with water, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:5→1:4), and recrystallized from ethyl acetate/n-hexane to give 6-fluoro-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.12 g) and 6-fluoro-1-(4-[bis-(3,5-dichlorobenzoyl)amino]-benzoyl}-1,2,3,4-tetrahydroquinoline.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitfurther, at room temperature for 1 hour
  4. stirringThe mixture is stirred at room temperature for 4 hours
  5. washThe reaction mixture is washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:5→1:4)
  9. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-7eac699b08d34f0bbc5e530cd1062ef9
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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