Sodium Dithionite → 3-(4-aminophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate

HRID 1188258Notes

Reaction equation

HRID 1188258 reaction equation
[F:1][C:2]([F:28])([F:27])[S:3]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:26])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)=[CH:13][O:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1>[F:28][C:2]([F:1])([F:27])[S:3]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:26])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)=[CH:13][O:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 24489Sodium Dithionite2×HCID 866950523-(4-nitrophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate

Product 1

HCID 866950533-(4-aminophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonateYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-(4-nitrophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate (5.0 g, 14.75 mmol) in tetrahydrofuran (20 mL) was added a freshly prepared solution of sodium dithionite (5.13 g in 20 mL). The mixture was stirred at room temperature for 2 hours and then additional sodium dithionite (2.57 g) was added in two portions. The reaction mixture was stirred for 24 hours at room temperature, after which time the reaction was complete. The organic solvent was evaporated under reduced pressure and then water (10 mL) was added to the suspension. The solids in suspension were filtered off and dried under high vacuum. The product was heated with acetonitrile and stirred until room temperature was achieved. The solids were filtered off to provide 3-(4-aminophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate (4.1 g), which was used in the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred for 24 hours at room temperature
  2. customThe organic solvent was evaporated under reduced pressure
  3. additionwater (10 mL) was added to the suspension
  4. filtrationThe solids in suspension were filtered off
  5. customdried under high vacuum
  6. temperatureThe product was heated with acetonitrile
  7. stirringstirred until room temperature
  8. filtrationThe solids were filtered off

Sources & evidence

ORD record
ord-19b83dfdded045d39e735b67afa6881b
Source dataset
uspto-grants-2014_03
Patent number
US08673966B2

Reaction notes

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