HCID 22405126, compound → HCID 22405137, compound

HRID 441244Notes

Reaction equation

HRID 441244 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:37]=[CH:36][CH:35]=[CH:34][C:12]=1[C:13]([NH:15][C:16]1[CH:33]=[CH:32][C:19]([C:20]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1)=[O:14])=[N+]=[N-].[H][H]>CO.O1CCOCC1.[Pd]>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:37]=[CH:36][CH:35]=[CH:34][C:12]=1[C:13]([NH:15][C:16]1[CH:33]=[CH:32][C:19]([C:20]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1)=[O:14]

Participants

6

Reactant 2

HCID 22405126HCID 22405126, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22405137HCID 22405137, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-[4-[2-(2-azidomethylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (535 mg) in a mixture of methanol (35 ml) and dioxane (4 ml) containing catalytic palladium on carbon (60 mg) was stirred under atmospheric pressure of hydrogen at ambient temperature. After 3 hours, the reaction mixture was filtered through a bed of celite, and then concentrated to give 1-{4-[2-(2-aminomethylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (395 mg) which was purified by recrystallization from a mixture of ethyl acetate and diethyl ether.

Workup

  1. filtrationthe reaction mixture was filtered through a bed of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-576e3175bd70432eaad9ae854927d23a
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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