5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one → 5-Amino-2,3-dihydro-1,3-benzoxazol-2-one

HRID 2362271Notes

Reaction equation

HRID 2362271 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1

Participants

4

Reactant 1

HCID 2639655-Nitro-2,3-dihydro-1,3-benzoxazol-2-one

Product 1

HCID 268565-Amino-2,3-dihydro-1,3-benzoxazol-2-oneYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of 39-1 (5.1 g, 28.31 mmol), Pd/C (0.5 g) and HCO2NH4 (8.9 g, 141.57 mmol) in MeOH (200 mL) was stirred at room temperature overnight. Filtered with kiselguhr, concentrated in vacuo, the residue was added 5% NaHCO3 solution, collected the solid and washed with water (50 mL), dried in vacuo to get compound 39-2 as a brown solid (4 g, yield 94%).

Workup

  1. filtrationFiltered with kiselguhr
  2. concentrationconcentrated in vacuo
  3. additionthe residue was added 5% NaHCO3 solution
  4. customcollected the solid
  5. washwashed with water (50 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-34778f8a1f814a9e8c2526ac1c6c73bf
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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