5-Chloro-7-nitro-2,3-dihydro-1,3-benzoxazol-2-one → 7-Amino-2(3H)-benzoxazolone

HRID 656378Notes

Reaction equation

HRID 656378 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1>CCO.[Pd]>[NH2:12][C:4]1[C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=[CH:2][CH:3]=1

Participants

4

Reactant 1

HCID 299761115-Chloro-7-nitro-2,3-dihydro-1,3-benzoxazol-2-one

Product 1

HCID 111478147-Amino-2(3H)-benzoxazolone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-chloro-7-nitro-1,3-benzoxazol-2(3H)-one from Step A (1.10 g, 5.13 mmol) in EtOH (50 mL) was added 10% Pd/C (300 mg). The reaction mixture was shaken in a Parr aparatus under a hydrogen atmosphere (40 p.s.i.) for 18 h, then filtered through a Celite pad, washing with EtOH, and the filtrate was concentrated under reduced pressure to give the title compound. MS: m/z=151 (M+1).

Workup

  1. filtrationfiltered through a Celite pad
  2. washwashing with EtOH
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a28a9125f1e14bdd92cf528505611527
Source dataset
uspto-grants-2011_12
Patent number
US08071770B2

Reaction notes

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