Hydrochloric Acid → 4,5-Diamino-2',7'-difluoro-3',6'-dihydroxy-spiro[isobenzofuran-1(3H),9'-[9H]-xanthen]-3-one

HRID 413881Notes

Reaction equation

HRID 413881 reaction equation
[NH2:1][C:2]1[C:27]([N+:28]([O-])=O)=[CH:26][CH:25]=[C:24]2[C:3]=1[C:4](=[O:31])[O:5][C:6]12[C:19]2[CH:18]=[C:17]([F:20])[C:16]([OH:21])=[CH:15][C:14]=2[O:13][C:12]2[C:7]1=[CH:8][C:9]([F:23])=[C:10]([OH:22])[CH:11]=2.Cl>>[NH2:1][C:2]1[C:27]([NH2:28])=[CH:26][CH:25]=[C:24]2[C:3]=1[C:4](=[O:31])[O:5][C:6]12[C:7]2[CH:8]=[C:9]([F:23])[C:10]([OH:22])=[CH:11][C:12]=2[O:13][C:14]2[C:19]1=[CH:18][C:17]([F:20])=[C:16]([OH:21])[CH:15]=2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 130077224-Amino-5-nitro-2',7'-difluoro-3',6'-dihydroxy-spiro [isobenzofuran-1(3h),9'-[9h]xanthen]-3-one

Product 1

HCID 130077234,5-Diamino-2',7'-difluoro-3',6'-dihydroxy-spiro[isobenzofuran-1(3H),9'-[9H]-xanthen]-3-oneYield 78.7%

Procedure

4-Amino-5-nitro-2′,7′-difluoro-3′,6′-dihydroxy-spiro[isobenzofuran-1(3H),9′-[9H]xanthen]-3-one (1.3 g, 3.0 mmol) was added to an aqueous solution of Na2S and NaSH, and the mixture was refluxed for 24 hours. The reaction mixture was cooled, and adjusted to pH 3 with hydrochloric acid, and precipitates were collected by filtration. The obtained product was dried and purified by silica gel chromatography to obtain the title compound (0.94 g, 78%).

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. customprecipitates
  4. filtrationwere collected by filtration
  5. customThe obtained product was dried
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a1108f67794f426f8a8f2290a24176b5
Source dataset
uspto-grants-2003_05
Patent number
US06569892B2

Reaction notes

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