5-Fluoro-6-nitro-2,3-dihydro-1,3-benzoxazol-2-one → 6-Amino-5-fluoro-2,3-dihydro-1,3-benzoxazol-2-one

HRID 1886150Notes

Reaction equation

HRID 1886150 reaction equation
[F:1][C:2]1[C:3]([N+:12]([O-])=O)=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1>O1CCCC1.[C].[Pd]>[NH2:12][C:3]1[C:2]([F:1])=[CH:11][C:6]2[NH:7][C:8](=[O:10])[O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 112178355-Fluoro-6-nitro-2,3-dihydro-1,3-benzoxazol-2-one

Product 1

HCID 156759596-Amino-5-fluoro-2,3-dihydro-1,3-benzoxazol-2-oneYield 107.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-fluoro-6-nitro-2(3H)-benzoxazolone (20 g, 0.1 mole) in 300 ml tetrahydrofuran was added 2 g palladium carbon (5%) under nitrogen atmosphere. The mixture was hydrogenated with a Parr shaker for 10 hours at 45 psi. The precipitate which resulted from hydrogenation was redissolved by adding tetrahydrofuran. The catalyst was removed by filtration and the filtrate was concentrated to give 18.1 g of the title compound as a brown solid: m.p. 180°-182° C. (dec.).

Workup

  1. customThe precipitate which resulted from hydrogenation
  2. dissolutionwas redissolved
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8c23a550a38c457c85ee5b7ec5c093fb
Source dataset
uspto-grants-1992_09
Patent number
US05149821

Reaction notes

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