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

HRID 1665630Notes

Reaction equation

HRID 1665630 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 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (50 mg) was added to a stirred solution of 5-nitro-3H-benzooxazol-2-one (450 mg, 2.5 mmol) in MeOH (5 mL) added under an atmosphere of hydrogen and the mixture was stirred for 3 hours. The mixture was then filtered over celite and the filtrate was evaporated to afford 380 mg (95%) of 5-amino-3H-benzooxazol-2-one. 1H NMR: (DMSO-d6): δ 6.88 (d, 1H), 6.3 (d, 1H), 6.22 (dd, 1H), 4.5 (s, 2H).

Workup

  1. additionadded under an atmosphere of hydrogen
  2. filtrationThe mixture was then filtered over celite
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-3463342441b14ea4a1d10a9d48e726df
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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