4-Nitro-3-(tetrahydrofuran-3-yloxy)-benzamide → 4-Amino-3-(tetrahydrofuran-3-yloxy)-benzamide

HRID 472017Notes

Reaction equation

HRID 472017 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][C:5]=1[O:13][CH:14]1[CH2:18][CH2:17][O:16][CH2:15]1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][C:5]=1[O:13][CH:14]1[CH2:18][CH2:17][O:16][CH2:15]1

Participants

4

Reactant 1

HCID 592259634-Nitro-3-(tetrahydrofuran-3-yloxy)-benzamide

Product 1

HCID 592259644-Amino-3-(tetrahydrofuran-3-yloxy)-benzamideYield 104.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-nitro-3-(tetrahydrofuran-3-yloxy)-benzamide (4.77 g, 18.15 mmol) in ethanol (200 ml) was added 10% palladium on carbon (0.5 g, 10% w/w) and the flask rinsed with an additional portion of ethanol (20 ml). The reaction was then purged with a nitrogen atmosphere, placed under a H2 (g) atmosphere and stirred at room temperature for 18 hours. The reaction was then purged with N2 (g) and filtered through a celite pad. The pad was washed with ethanol (100 ml) and the filtrate concentrated to dryness in vacuo to give the title compound as a white solid (4.22 g, 18.9 mmol, 100% corrected). LCMS: [M+H]+=223, Rt=1.01 min, 100% purity

Workup

  1. washthe flask rinsed with an additional portion of ethanol (20 ml)
  2. customThe reaction was then purged with a nitrogen atmosphere
  3. customThe reaction was then purged with N2 (g)
  4. filtrationfiltered through a celite pad
  5. washThe pad was washed with ethanol (100 ml)
  6. concentrationthe filtrate concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-59d595e5ea21420b91ff3bcec5562e6f
Source dataset
uspto-grants-2014_01
Patent number
US08633201B2

Reaction notes

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