HCID 10501216, compound → HCID 19607806, compound

HRID 1603092Notes

Reaction equation

HRID 1603092 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[C:7]([NH:9][C:10]1[CH:27]=[CH:26][C:13]([C:14]([N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:12][CH:11]=1)=[O:8])([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[C:7]([NH:9][C:10]1[CH:27]=[CH:26][C:13]([C:14]([N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:12][CH:11]=1)=[O:8]

Participants

5

Reactant 2

HCID 10501216HCID 10501216, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19607806HCID 19607806, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethanol (50 ml) is added to 10% Pd-C (0.1 g) and thereto is added 1-[4-(3-nitrobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.73 g). The mixture is subjected to catalytic reduction at ordinary temperature under atmospheric pressure of hydrogen. After completion of the reduction, 10% Pd-C is removed by filtration and the filtrate is concentrated under reduced pressure. The residue is extracted with dichloromethane and the extract is dried over magnesium sulfate. The solvent is distilled off under reduced pressure and recrystallized from methanol to give 1-[4-(3-aminobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.54 g) as white powder, m.p. 205.5-206.5° C.

Workup

  1. customAfter completion of the reduction, 10% Pd-C is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. extractionThe residue is extracted with dichloromethane
  4. dry with materialthe extract is dried over magnesium sulfate
  5. distillationThe solvent is distilled off under reduced pressure
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4b783f0aedb9465a940c307ea912ab1f
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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