Acetic Acid → Flumioxazin

HRID 235577Notes

Reaction equation

HRID 235577 reaction equation
[NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][C:13]#[CH:14])[C:6]=2[CH:15]=1.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2[CH2:23][CH2:24][CH2:25][CH2:26][C:18]1=2.C(O)(=O)C>O>[F:16][C:3]1[C:2]([N:1]2[C:20](=[O:21])[C:19]3[CH2:23][CH2:24][CH2:25][CH2:26][C:18]=3[C:17]2=[O:22])=[CH:15][C:6]2[N:7]([CH2:12][C:13]#[CH:14])[C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 111603236-amino-7-fluoro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 92425FlumioxazinYield 24.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-amino-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.31 g), 3,4,5,6-tetrahydrophthalic anhydride (0.28 g) and acetic acid (3 ml) was heated under reflux for 2 hours. After being allowed to cool, water was added to the mixture, which was then extracted with ethyl acetate. The organic layer was washed with water, neutralized with sodium bicarbonate solution, dried and concentrated. The residue was purified by silica gel thin layer chromatography using a mixture of ethyl acetate and hexane (1:2) as an eluent to give 2-[7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.12 g). m.p., 196.0° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel thin layer chromatography
  9. additiona mixture of ethyl acetate and hexane (1:2) as an eluent

Sources & evidence

ORD record
ord-95c5e1d113544d9499ac01036af8e0a4
Source dataset
uspto-grants-1987_02
Patent number
US04640707

Reaction notes

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