HCID 44571372, compound → N-[(5-amino-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide

HRID 551113Notes

Reaction equation

HRID 551113 reaction equation
[OH:1][C:2]1[C:3]([CH:15]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:16][C:17](=[O:26])[CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2>C1COCC1.[Pd]>[NH2:12][C:5]1[CH:4]=[C:3]([CH:15]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:16][C:17](=[O:26])[CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

4

Reactant 1

HCID 44571372HCID 44571372, compound

Product 1

HCID 67171864N-[(5-amino-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamideYield 61.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-[(8-hydroxy-5-nitroquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide (4.0 g, 9.31 mmol), 10% Pd/C (420 mg) in 70 ml THF were hydrogenated at 42 psi for 20 h. The reaction mixture was filtered through Celite 545, dried over sodium sulfate and concentrated to afford 2.3 g of N-[(5-amino-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide as a brown foam.

Workup

  1. filtrationThe reaction mixture was filtered through Celite 545
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-39bd156d5c544ea9a06ebb669c11477d
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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