HCID 15538683, compound → HCID 15538684, compound

HRID 1597179Notes

Reaction equation

HRID 1597179 reaction equation
[F:1][C:2]1[C:13]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:12]([N+:27]([O-])=O)[C:5]2[N:6]([CH3:11])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1>C(O)(=O)C.[Fe]>[NH2:27][C:12]1[C:5]2[N:6]([CH3:11])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=[C:2]([F:1])[C:13]=1[N:14]1[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]1=[O:26]

Participants

4

Reactant 1

HCID 15538683HCID 15538683, compound

Product 1

HCID 15538684HCID 15538684, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

3-[7-Fluoro-4-methyl-5-nitro-2H-1,4-benzoxazine-3(4H)-on-6-yl]-1-methyl-6-trifluoromethyl-2,4-(1H, 3H)-pyrimidinedione (1.45 g) was dissolved in acetic acid (80 ml) containing iron powder (1.16 g). The mixture was stirred for 3 days under nitrogen atmosphere. After filtration, water (100 ml) and ethyl acetate (150 ml) were added to the filtrate, the organic phase was washed with water (30 ml×3) and brine (30 ml), dried over sodium sulfate. After filtration and evaporation, the residue was purified by silica gel column (hexane to 40% ethyl acetate) to afford the title compound (1.1 g).

Workup

  1. filtrationAfter filtration, water (100 ml) and ethyl acetate (150 ml)
  2. additionwere added to the filtrate
  3. washthe organic phase was washed with water (30 ml×3) and brine (30 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and evaporation
  6. customthe residue was purified by silica gel column (hexane to 40% ethyl acetate)

Sources & evidence

ORD record
ord-9c5fe7557a40483694ce24e1dddde8d2
Source dataset
uspto-grants-2001_09
Patent number
US06294503B1

Reaction notes

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