HCID 24960377, compound → HCID 67172478, compound

HRID 551108Notes

Reaction equation

HRID 551108 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([C:22]2[C:31]([OH:32])=[C:30]3[C:25]([CH:26]=[CH:27][CH:28]=[N:29]3)=[C:24]([Cl:33])[CH:23]=2)[NH:11][C:12](=[O:21])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]([C:22]2[C:31]([OH:32])=[C:30]3[C:25]([CH:26]=[CH:27][CH:28]=[N:29]3)=[C:24]([Cl:33])[CH:23]=2)[NH:11][C:12](=[O:21])[CH2:13][O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 24960377HCID 24960377, compound

Product 1

HCID 67172478HCID 67172478, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[(3-nitrophenyl)(5-chloro-8-hydroxyquinolin-7-yl)methyl]-2-phenoxyacetamide (2 g, 4.31 mmol) and 10% Pd/C (250 mg, Lancaster) in THF was hydrogenated for 20 h at 40 psi. The catalyst was filtered off, and solvent was removed under vacuum. The residue was triturated with ether, filtered and the cake was washed with ether to give 1.1 g of N-[(3-aminophenyl)(5-chloro-8-hydroxyquinolin-7-yl)methyl]-2-phenoxyacetamide as an off-white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customsolvent was removed under vacuum
  3. customThe residue was triturated with ether
  4. filtrationfiltered
  5. washthe cake was washed with ether

Sources & evidence

ORD record
ord-fe878fd029734f1eafe63016e4180b4a
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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