Ethyl 2,4-dinitro-5-fluorophenoxyacetate → 7-Fluoro-6-amino-2H-1,4-benzoxazin-3(4H)-one

HRID 1381643Notes

Reaction equation

HRID 1381643 reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]([N+:17]([O-])=O)[C:14]([F:20])=[CH:13][C:5]=1[O:6][CH2:7][C:8](OCC)=[O:9])([O-])=O.[H][H]>C(O)C.[C].[Pd]>[F:20][C:14]1[C:15]([NH2:17])=[CH:16][C:4]2[NH:1][C:8](=[O:9])[CH2:7][O:6][C:5]=2[CH:13]=1

Participants

5

Reactant 2

HCID 14423667Ethyl 2,4-dinitro-5-fluorophenoxyacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 103133897-Fluoro-6-amino-2H-1,4-benzoxazin-3(4H)-oneYield 82.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A suspension of ethyl 2,4-dinitro-5-fluorophenoxyacetate (1.3 g) and 5% palladium-carbon (0.35 g) in ethanol (30 ml) was subjected to catalytic reduction at room temperature under an ordinary pressure until 600 ml of hydrogen was absorbed. The reaction mixture was filtered, and the filtrate was concentrated to give 7-fluoro-6-amino-2H-1,4-benzoxazin-3(4H)-one (0.68 g; yield, 82.8%).

Workup

  1. customwas absorbed
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-92e17dc7626b4ac49c68a069184d8e04
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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