Sodium hydrosulfide hydrate → 8-amino-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one

HRID 876521Notes

Reaction equation

HRID 876521 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)=[CH:10][C:9]2=[O:24])([O-])=O.O.[SH-].[Na+]>CO.O>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=1)=[CH:10][C:9]2=[O:24]

Participants

5

Reactant 2

HCID 16211346Sodium hydrosulfide hydrateHCID 584772368-nitro-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one

Product 1

HCID 584772718-amino-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-oneYield 87.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

8-nitro-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one 2 (300 mg, 0.90 mmol) was taken up in 10 mL of MeOH. Sodium hydro sulfide hydrate (250 mg, 4.5 mol) was added as a solution in 4 mL of H2O. The reaction mixture was stirred under reflux for 45 min. It was then cooled to room temperature and concentrated under reduced pressure. The resulting aqueous mixture was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford 240 mg of 178. MS (ESI) calcd for C16H10F3NO2: 305.07. found: 306 [M+H].

Workup

  1. temperatureunder reflux for 45 min
  2. concentrationconcentrated under reduced pressure
  3. extractionThe resulting aqueous mixture was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39dbee5e19484327b7e26c32f6432c22
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

Loading…