Methanesulfonic Acid → 4-Amino-5-nitro-2',7'-difluoro-3',6'-dihydroxy-spiro [isobenzofuran-1(3h),9'-[9h]xanthen]-3-one

HRID 413880Notes

Reaction equation

HRID 413880 reaction equation
C([NH:4][C:5]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:7]2[C:8]([O:10][C:11](=[O:12])[C:6]=12)=O)(=O)C.[F:19][C:20]1[CH:26]=[CH:25][C:23]([OH:24])=[CH:22][C:21]=1[OH:27].CS(O)(=O)=O>O>[NH2:4][C:5]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:7]2[C:6]=1[C:11](=[O:12])[O:10][C:8]12[C:25]2[CH:26]=[C:20]([F:19])[C:21]([OH:27])=[CH:22][C:23]=2[O:24][C:23]2[C:25]1=[CH:26][C:20]([F:19])=[C:21]([OH:27])[CH:22]=2

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 105586404-Fluoro-1,3-dihydroxybenzeneHCID 155118353-Acetamido-4-nitrophthalic anhydride

Product 1

HCID 130077224-Amino-5-nitro-2',7'-difluoro-3',6'-dihydroxy-spiro [isobenzofuran-1(3h),9'-[9h]xanthen]-3-oneYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3-Acetamido-4-nitrophthalic anhydride (1.3 g, 5.0 mmol) and 4-fluororesorcinol (1.3 g, 10 mmol) were added to methanesulfonic acid (10 ml), and the mixture was stirred at 80° C. under an argon atmosphere for 60 hours. The reaction mixture was added with water (120 ml) and refluxed for 2 hours. The reaction mixture was adjusted to pH 2, and precipitates were collected by filtration. The obtained product was dried and purified by silica gel chromatography (3% methanol/97% dichloromethane, v/v) to obtain the title compound (1.3 g, 61%).

Workup

  1. temperaturerefluxed for 2 hours
  2. customprecipitates
  3. filtrationwere collected by filtration
  4. customThe obtained product was dried
  5. custompurified by silica gel chromatography (3% methanol/97% dichloromethane, v/v)

Sources & evidence

ORD record
ord-e6752064b5b8418fae31b48e73a80f1e
Source dataset
uspto-grants-2003_05
Patent number
US06569892B2

Reaction notes

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