6-Amino-3,3-dimethylindan-1-one → 6-Hydroxy-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

HRID 53279Notes

Reaction equation

HRID 53279 reaction equation
N([O-])=[O:2].[Na+].N[C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:17])([CH3:16])[CH2:11][C:12]2=[O:15])=[CH:8][CH:7]=1>O.F[B-](F)(F)F.[H+]>[OH:2][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:17])([CH3:16])[CH2:11][C:12]2=[O:15])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 124417896-Amino-3,3-dimethylindan-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 193658996-Hydroxy-3,3-dimethyl-2,3-dihydro-1H-inden-1-oneYield 50.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 28118Tetrafluoroboric acidSolvent

Procedure

A solution of sodium nitrite (14.8 g, 214 mmol) in 30 mL of water was slowly added to the solution of 6-amino-3,3-dimethyl-indan-1-one (14.0 g, 85.8 mmol) in 30 mL of 48% tetrafluoroboric acid and 30 mL of water at 0°-5° C. After being stirred for 30 min, the mixture was filtered, and the solids were washed with cold 5% tetrafluoroboric acid and dried in vacuum. The solids were then added in several portions into a boiling solution of 50 mL of sulfuric acid in 0.5 liter of water. After refluxing for 1 hour, the solution was cooled to room temperature and extracted with ethyl acetate (100 mL×3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (EtOAc:hexane=1:10 to 1:2) to give 7.60 g (50% yield) of the title compound as a solid; 1H-NMR (CDCl3) δ1.40 (s, 6H), 2.64 (s, 2H), 7.13 (s, 1H),7.18 (d, J=8.2 Hz, 1H), 7.39 (d, J=8.2 Hz, 1H); MS m/e 177 (MH+).

Workup

  1. filtrationthe mixture was filtered
  2. washthe solids were washed with cold 5% tetrafluoroboric acid
  3. customdried in vacuum
  4. additionThe solids were then added in several portions into a boiling solution of 50 mL of sulfuric acid in 0.5 liter of water
  5. temperatureAfter refluxing for 1 hour
  6. extractionextracted with ethyl acetate (100 mL×3)
  7. dry with materialThe combined extracts were dried over magnesium sulfate
  8. customevaporated
  9. customThe residue was purified by flash chromatography (EtOAc:hexane=1:10 to 1:2)

Sources & evidence

ORD record
ord-d863d2c7169d4eaa9fad627b62a0ac69
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Reaction notes

Loading…