2-(5-Fluoro-2,4-dinitrophenoxy)acetic acid → 7-Fluoro-6-amino-2H-1,4-benzoxazin-3(4H)-one

HRID 1381641Notes

Reaction equation

HRID 1381641 reaction equation
[N+:1]([C:4]1[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([F:18])=[CH:11][C:5]=1[O:6][CH2:7][C:8](O)=[O:9])([O-])=O.[H][H]>C(O)C.[C].[Pd]>[F:18][C:12]1[C:13]([NH2:15])=[CH:14][C:4]2[NH:1][C:8](=[O:9])[CH2:7][O:6][C:5]=2[CH:11]=1

Participants

5

Reactant 2

HCID 3028912-(5-Fluoro-2,4-dinitrophenoxy)acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 103133897-Fluoro-6-amino-2H-1,4-benzoxazin-3(4H)-oneYield 92.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2,4-dinitro-5-fluorophenoxyacetic acid (2.0 g) and 10% palladium-carbon (hydrated) (1.0 g) in ethanol (30 ml) was subjected to catalytic reduction at room temperature under an ordinary pressure until 1000 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 (1.3 g; yield, 92.8%).

Workup

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

Sources & evidence

ORD record
ord-4ab8a39e86974fadbf694afc80990fda
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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