3-Nitro-7-(5-methyl-2-phenyl-4-oxazolylmethoxy)quinoline → 3-Amino-7-(5-methyl-2-phenyl-4-oxazolylmethoxy)quinoline

HRID 1938340Notes

Reaction equation

HRID 1938340 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=1[CH3:21])[CH:8]=2)([O-])=O>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=1[CH3:21])[CH:8]=2

Participants

5

Reactant 1

HCID 214693263-Nitro-7-(5-methyl-2-phenyl-4-oxazolylmethoxy)quinoline

Product 1

HCID 214692703-Amino-7-(5-methyl-2-phenyl-4-oxazolylmethoxy)quinolineYield 42%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture of ethanol (20 mL) and ethyl acetate (10 mL) was suspended 3-nitro-7-(5-methyl-2-phenyl-4-oxazolylmethoxy)quinoline (740 mg, 2.1 mmol.), and to the suspension was added 10% palladium/carbon (50 mg). Then, catalytic reduction was performed overnight. After the completion of reaction was confirmed, the reaction mixture was filtered over Celite®, and the filtrate was placed under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/7 to ethyl acetate), to give 280 mg of the desired compound as brown oil (yield 42%).

Workup

  1. customAfter the completion of reaction
  2. filtrationthe reaction mixture was filtered over Celite®
  3. customto remove the solvent
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/7 to ethyl acetate)

Sources & evidence

ORD record
ord-35bc5fa6f6db4664859e78d18e822f26
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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